[ CAS No. 6134-53-8 ] {[proInfo.proName]}

Name: 6134-53-8|4-Bromo-2,3-dihydro-1H-indene|95%
Brand: Ambeed
SKU: A353241
Price: 41.0 USD
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2D 3D

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Quality Control of [ 6134-53-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6134-53-8 ]

SDS Specification

Alternatived Products of [ 6134-53-8 ]

Product Details of [ 6134-53-8 ]

CAS No. :	6134-53-8	MDL No. :	MFCD22059711
Formula :	C₉H₉Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JCQMGSFTMQWFPE-UHFFFAOYSA-N
M.W :	197.07	Pubchem ID :	11745586
Synonyms :

Calculated chemistry of [ 6134-53-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.77
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.44
Log Po/w (XLOGP3) :	3.45
Log Po/w (WLOGP) :	2.94
Log Po/w (MLOGP) :	3.59
Log Po/w (SILICOS-IT) :	3.81
Consensus Log Po/w :	3.25

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.68
Solubility :	0.0412 mg/ml ; 0.000209 mol/l
Class :	Soluble
Log S (Ali) :	-3.13
Solubility :	0.146 mg/ml ; 0.000739 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.08
Solubility :	0.0163 mg/ml ; 0.0000826 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.91

Safety of [ 6134-53-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6134-53-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 6134-53-8 ]
Downstream synthetic route of [ 6134-53-8 ]

[ 6134-53-8 ] Synthesis Path-Upstream 1~16

1
[ 15115-60-3 ]
[ 6134-53-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylsilane; trifluoroacetic acid In tetrahydrofuran; dichloromethane at -20 - 20℃; for 2 h;	To a solution of 4-bromo-2,3-dihydro-lH-inden-l-one (2 g, 10 mmol) in DCM (lOmL) was added TFA, then cooled to - 20°C. Et₃SiH (15 ml_, IN in THF, 15 mmol) was added drop wise. After stirring for 2h at RT the reaction mixture was poured into NH₄CI aqueous and extracted with DCM (10 ml_2), washed with brine (10 ml_2), dried by MgS0₄, concentrated, purified by FC to afford compound (1.7 g, yield : 85percent); m/z (ES+) : 197 [M + H] ⁺
80%	With triethylsilane; trifluorormethanesulfonic acid In dichloromethane at 0 - 20℃; for 16 h;	To a solution of 4-bromoindan-1-one (200 mg, 947 umol) in dichloromethane (10 mL) was added a solution of trifluoromethanesulfonic acid (426 mg, 2.84 mmol) in dichloromethane (500 uL) and the reaction mixture was cooled to 0 °C. Then triethylsilane (220 mg, 1.90 mmol) in dichloromethane (500 uL) was added dropwise to the reaction mixture and the mixture was stirred at 0 °C for 0.5 hr. TLC detected most starting material remained. Then another batch of trifluoromethanesulfonic acid (426 mg, 2.84 mmol) and triethylsilane (220 mg, 1.90 mmol) was added in turn and the reaction mixture was stirred at 20 °C for 15.5 hrs. On completion, the reaction mixture was diluted with 15 mL DCM and washed with saturated sodium bicarbonate until pH = 7. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether) to give the title compound (1.00 g, 80percent yield) as colorless oil.¹H NMR (400MHz, CDCl3) δ = 7.31 (d, J = 7.6 Hz, 1H), 7.16 (d, J = 7.6 Hz, 1H), 7.02 (dd, J = 7.6, 7.6 Hz, 1H), 3.04 (t, J = 7.2 Hz, 2H), 2.98 (t, J = 7.2 Hz, 2H), 2.11 (m, 2H).

Reference： [1] Patent: WO2015/24878, 2015, A1, . Location in patent: Page/Page column 110
[2] Patent: WO2018/106636, 2018, A1, . Location in patent: Paragraph 00232
[3] Journal of the Chemical Society, 1939, p. 794,797
[4] Journal of the American Chemical Society, 1935, vol. 57, p. 2174
[5] Bulletin of the Chemical Society of Japan, 1961, vol. 34, p. 1189 - 1194
[6] Bulletin de la Societe Chimique de France, 1966, p. 3618 - 3625

2
[ 32202-61-2 ]
[ 6134-53-8 ]

Yield	Reaction Conditions	Operation in experiment
15%	Stage #1: With tetrafluoroboric acid; sodium nitrite In water for 0.333333 h; Cooling with ice Stage #2: With copper(ll) bromide In dimethyl sulfoxide for 0.5 h;	Step 1 : 4-BromoindanTo a thick mixture of 4-aminoindan (2.66 g, 20 mmol) in 48percent tetrafluoroboric acid (20 ml) cooled in an ice bath was added a solution of sodium nitrite (1.6 g, 23 mmol) in water (20 ml) over 10 minutes. The mixture was stirred in ice for 10 minutes and was filtered and the filter cake was washed with cold 5percent tetrafluoroboric acid (10 ml) and then with cold water (10 ml). The filter cake was added in portions to copper (II) bromide (5.6 g, 25 mmol) in dimethyl sulfoxide (50 ml). The mixture was stirred for 30 minutes and was added to water (150ml). The mixture was extracted with ethyl acetate (150 ml) and the organic layer was washed with water. The organic layer was dried over magnesium sulfate and was filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using heptane to give the title compound (0.6g, 15percent).

Reference： [1] Patent: WO2011/34828, 2011, A1, . Location in patent: Page/Page column 44

3
[ 496-11-7 ]
[ 6134-53-8 ]
[ 6134-54-9 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1983, vol. 2, # 3-4, p. 96 - 104
[2] Journal of the American Chemical Society, 1941, vol. 63, p. 301
[3] Journal of Organic Chemistry, 1988, vol. 53, # 19, p. 4531 - 4534
[4] Patent: US2012/209005, 2012, A1, . Location in patent: Page/Page column 32

4
[ 496-11-7 ]
[ 6134-53-8 ]
[ 6134-54-9 ]

Reference： [1] Patent: US2006/270686, 2006, A1, . Location in patent: Page/Page column 27
[2] Patent: US2008/280891, 2008, A1, . Location in patent: Page/Page column 27

5
[ 496-11-7 ]
[ 6134-53-8 ]

Reference： [1] Synthetic Communications, 1992, vol. 22, # 8, p. 1095 - 1099

6
[ 1643-26-1 ]
[ 6134-53-8 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 432 - 433

7
[ 18944-77-9 ]
[ 6134-53-8 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 432 - 433

8
[ 76727-24-7 ]
[ 6134-53-8 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 432 - 433

9
[ 166949-93-5 ]
[ 6134-53-8 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 432 - 433

10
[ 15115-58-9 ]
[ 6134-53-8 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1961, vol. 34, p. 1189 - 1194
[2] Bulletin de la Societe Chimique de France, 1966, p. 3618 - 3625
[3] Patent: WO2018/106636, 2018, A1,

11
[ 90725-40-9 ]
[ 6134-53-8 ]

Reference： [1] Journal of the Chemical Society, 1939, p. 794,797
[2] Bulletin of the Chemical Society of Japan, 1961, vol. 34, p. 1189 - 1194

12
[ 95-46-5 ]
[ 6134-53-8 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1961, vol. 34, p. 1189 - 1194

13
[ 66192-11-8 ]
[ 6134-53-8 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1961, vol. 34, p. 1189 - 1194

14
[ 3433-80-5 ]
[ 6134-53-8 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1961, vol. 34, p. 1189 - 1194

15
[ 201486-97-7 ]
[ 6134-53-8 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 432 - 433

16
[ 496-11-7 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 6134-53-8 ]
[ 6134-54-9 ]

Reference： [1] Journal of the American Chemical Society, 1941, vol. 63, p. 301

[ 6134-53-8 ] Synthesis Path-Downstream 1~70

1
[ 496-11-7 ]
[ 6134-53-8 ]
[ 6134-54-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzyltrimethylazanium tribroman-2-uide; zinc dibromide; In acetic acid; at 20℃; for 4h;	Reference Synthetic Example 51-[5-(2,3-Dihydro-1H-inden-5-yl)-4-hydroxythiophen-3-yl]ethanone(1) Synthesis of (2,3-dihydro-1H-inden-5-yl)boronic acid Synthesis was carried out by the following synthesis methods 3 and 4.Synthesis Method 35.91 g (0.05 mol) of 2,3-dihydro-1H-indene was stirred with 60 ml of acetic acid at room temperature, and to the resulting solution, 12.3 g (0.055 mol) of zinc (II) bromide was added and then 19.5 g (0.05 mol) of benzyltrimethylammonium tribromide was added. After the addition, the reaction solution was stirred at room temperature for 4 hours to complete the reaction. After completion of the reaction, the reaction solution was extracted by adding ethyl acetate and saturated aqueous sodium chloride. The ethyl acetate layer was neutralized and washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane) to isolate 5.11 g of an oil (yield: 51.9%). The oil turned out to be a mixture of about 70 to 80% of the 5-bromide and about 30 to 20% of the 4-bromide upon 1H-NMR analysis. 8.3 g (0.0421 mol) of 5-bromo-2,3-dihydro-1H-indene and 4-bromo-2,3-dihydro-1H-indene was stirred with 40 ml of dry tetrahydrofuran with cooling to -78 C., and 32.0 ml of 1.6 M n-butyllithium in n-hexane was added dropwise. After the dropwise addition, the reaction solution was stirred at -78 C. for 15 minutes, and 8.75 g (0.0842 mol) of trimethyl borate was added. After the dropwise addition, the reaction solution was stirred for 3 hours while the temperature was allowed to elevate to -20 C. Then, 50 ml of 1 M hydrochloric acid was added dropwise, and the reaction solution was stirred for 2 hours while the temperature was allowed to elevate to room temperature. The reaction solution was extracted by adding 300 ml of ethyl acetate and 250 ml of saturated aqueous sodium chloride. The ethyl acetate layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the ethyl acetate was evaporated under reduced pressure. The residual crystals were stirred with 20 ml of ethyl acetate and dispersed by adding 150 ml of n-hexane. The crystals were collected by filtration, washed with n-hexane and dried to obtain 2.5 g of the desired product (yield: 36.7%).

Reference： [1]Bulletin de la Societe Chimique de France,1983,vol. 2,p. 96 - 104
[2]Journal of the American Chemical Society,1941,vol. 63,p. 301
[3]Journal of Organic Chemistry,1988,vol. 53,p. 4531 - 4534
[4]Patent: US2012/209005,2012,A1 .Location in patent: Page/Page column 32

2
[ 15115-60-3 ]
[ 6134-53-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylsilane; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; at -20 - 20℃; for 2h;	To a solution of 4-bromo-2,3-dihydro-lH-inden-l-one (2 g, 10 mmol) in DCM (lOmL) was added TFA, then cooled to - 20C. Et3SiH (15 ml_, IN in THF, 15 mmol) was added drop wise. After stirring for 2h at RT the reaction mixture was poured into NH4CI aqueous and extracted with DCM (10 ml_2), washed with brine (10 ml_2), dried by MgS04, concentrated, purified by FC to afford compound (1.7 g, yield : 85%); m/z (ES+) : 197 [M + H] +
80%	With triethylsilane; trifluorormethanesulfonic acid; In dichloromethane; at 0 - 20℃; for 16h;	To a solution of 4-bromoindan-1-one (200 mg, 947 umol) in dichloromethane (10 mL) was added a solution of trifluoromethanesulfonic acid (426 mg, 2.84 mmol) in dichloromethane (500 uL) and the reaction mixture was cooled to 0 C. Then triethylsilane (220 mg, 1.90 mmol) in dichloromethane (500 uL) was added dropwise to the reaction mixture and the mixture was stirred at 0 C for 0.5 hr. TLC detected most starting material remained. Then another batch of trifluoromethanesulfonic acid (426 mg, 2.84 mmol) and triethylsilane (220 mg, 1.90 mmol) was added in turn and the reaction mixture was stirred at 20 C for 15.5 hrs. On completion, the reaction mixture was diluted with 15 mL DCM and washed with saturated sodium bicarbonate until pH = 7. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether) to give the title compound (1.00 g, 80% yield) as colorless oil.1H NMR (400MHz, CDCl3) delta = 7.31 (d, J = 7.6 Hz, 1H), 7.16 (d, J = 7.6 Hz, 1H), 7.02 (dd, J = 7.6, 7.6 Hz, 1H), 3.04 (t, J = 7.2 Hz, 2H), 2.98 (t, J = 7.2 Hz, 2H), 2.11 (m, 2H).

Reference： [1]Patent: WO2015/24878,2015,A1 .Location in patent: Page/Page column 110
[2]Patent: WO2018/106636,2018,A1 .Location in patent: Paragraph 00232
[3]Journal of the Chemical Society,1939,p. 794,797
[4]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

3
[ 85-44-9 ]
[ 6134-53-8 ]
[ 93321-55-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

4
[ 529-19-1 ]
[ 6134-53-8 ]
[ 5385-29-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 401 - 402

5
[ 21382-98-9 ]
[ 6134-53-8 ]
[ 5385-33-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 401 - 402

6
[ 6609-56-9 ]
[ 6134-53-8 ]
[ 5385-31-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 401 - 402

7
[ 6134-53-8 ]
[ 544-92-3 ]
[ 15115-63-6 ]

Reference： [1]Bulletin de la Societe Chimique de France,1966,p. 3618 - 3625

8
[ 6134-53-8 ]
[ 100-47-0 ]
[ 5385-28-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 401 - 402

9
[ 6134-53-8 ]
[ 104-85-8 ]
[ 5385-30-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 401 - 402

10
[ 6134-53-8 ]
[ 874-90-8 ]
[ 5385-32-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 401 - 402

11
[ 496-11-7 ]
[ 6134-53-8 ]

Reference： [1]Synthetic Communications,1992,vol. 22,p. 1095 - 1099

12
[ 6134-53-8 ]
[ 74-88-4 ]
[ 824-22-6 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 4531 - 4534

13
[ 201486-97-7 ]
[ 6134-53-8 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 432 - 433

16
[ 496-11-7 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 6134-53-8 ]
[ 6134-54-9 ]

Reference： [1]Journal of the American Chemical Society,1941,vol. 63,p. 301

17
[ 6134-53-8 ]
aqueous KMnO₄ [ No CAS ]
[ 116-69-8 ]

Reference： [1]Journal of the American Chemical Society,1941,vol. 63,p. 301

18
[ 1643-26-1 ]
[ 6134-53-8 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 432 - 433

19
[ 18944-77-9 ]
[ 6134-53-8 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 432 - 433

20
[ 76727-24-7 ]
[ 6134-53-8 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 432 - 433

21
[ 446-52-6 ]
nPrMgHal [ No CAS ]
[ 6134-53-8 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 432 - 433

22
[ 166949-93-5 ]
[ 6134-53-8 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 432 - 433

23
[ 90725-40-9 ]
[ 6134-53-8 ]

Reference： [1]Journal of the Chemical Society,1939,p. 794,797
[2]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

24
[ 95-46-5 ]
[ 6134-53-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

25
[ 66192-11-8 ]
[ 6134-53-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

26
[ 15115-58-9 ]
[ 6134-53-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194
[2]Bulletin de la Societe Chimique de France,1966,p. 3618 - 3625
[3]Patent: WO2018/106636,2018,A1

27
[ 6134-53-8 ]
[ 641-48-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 401 - 402

28
[ 6134-53-8 ]
[ 63040-46-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

29
[ 6134-53-8 ]
[ 98801-50-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

30
[ 6134-53-8 ]
[ 97978-40-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

31
[ 6134-53-8 ]
[ 93319-37-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

32
[ 3433-80-5 ]
[ 6134-53-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1961,vol. 34,p. 1189 - 1194

33
[ 496-11-7 ]
C₉H₈Br₂ [ No CAS ]
[ 6134-53-8 ]
[ 6134-54-9 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum oxide; bromine;	Bromine (6.40 g, 40.0 mmol) adsorbed on alumina (30 g, neutral, Brockmann grade 1) was added to indane (4.70 g, 40.0 mmol) also adsorbed on alumina (30 g, neutral, Brockmann grade 1). The mixture was stirred until the color of the bromine disappeared (tlc showed completion). The reaction mixture was filtered through silica gel (100 g eluting with CH2Cl2) and the filtrate was concentrated in vacuo to provide the crude bromoindane (7.40 g) as a brown oil. The crude material was purified by flash chromatography (200 g SiO2, hexanes) to give a mixture of 2 mono-brominated indanes and a dibrominated indane (5.95 g, 68%) as yellow oil.
		Preparation of the Mixture of Boronic Acids. (According to Ranu, Synth. Comm. 1095 (1992) Bromine (6.40 g, 40.0 mmol) adsorbed on alumina (30 g, neutral, Brockmann grade 1) was added to indane (4.70 g, 40.0 mmol) also adsorbed on alumina (30 g, neutral, Brockmann grade 1). The mixture was stirred until the color of the bromine disappeared (tlc showed completion). The reaction mixture was filtered through silica gel (100 g eluting with CH2Cl2) and the filtrate was concentrated in vacuo to provide the crude bromoindane (7.40 g) as a brown oil. The crude material was purified by flash chromatography (200 g SiO2, hexanes) to give a mixture of 2 mono-brominated indanes and a dibrominated indane (5.95 g, 68%) as yellow oil.

Reference： [1]Patent: US2006/270686,2006,A1 .Location in patent: Page/Page column 27
[2]Patent: US2008/280891,2008,A1 .Location in patent: Page/Page column 27

34
[ 6134-53-8 ]
[ 6134-54-9 ]
[ 196861-31-1 ]
[ 915411-11-9 ]

Yield	Reaction Conditions	Operation in experiment
		An oven-dried flask was charged with the mixture of bromoindanes (340 mg, 1.73 mmol) and dry THF (2 mL) under argon. The solution was cooled to -78 C. and butyllithium (1.6 M in hexanes, 1.30 mL) was added drop-wise. The reaction mixture was stirred for 15 min at -78 C. and trimethyl borate (385 muL, 3.46 mmol) was added drop-wise. The reaction solution was left to warm to -20 C. over a period of 2.5 h and was then quenched with 1M aqueous HCl (2 mL). The mixture was left to warm to room temperature, was diluted with MTBE (20 mL) and the layers were separated. The organic layer was washed with H2O (5 mL) and brine 5 mL), dried (Na2SO4) and concentrated to give the crude boronic acid (232 mg). Flash chromatography (20 g SiO2, AcOEt/heptane 1:4?1:2) provided a mixture of 4- and 5-indane boronic acid (123 mg, 44%).

Reference： [1]Patent: US2006/270686,2006,A1 .Location in patent: Page/Page column 27

35
[ 121-43-7 ]
[ 6134-53-8 ]
[ 6134-54-9 ]
[ 196861-31-1 ]
[ 915411-11-9 ]

Yield	Reaction Conditions	Operation in experiment
		An oven-dried flask was charged with the mixture of bromoindanes (340 mg, 1.73 mmol) and dry THF (2 mL) under argon. The solution was cooled to -78 C. and butyllithium (1.6 M in hexanes, 1.30 mL) was added drop-wise. The reaction mixture was stirred for 15 min at -78 C. and trimethyl borate (385 muL, 3.46 mmol) was added drop-wise. The reaction solution was left to warm to -20 C. over a period of 2.5 h and was then quenched with 1M aqueous HCl (2 mL). The mixture was left to warm to room temperature, was diluted with MTBE (20 mL) and the layers were separated. The organic layer was washed with H2O (5 mL) and brine 5 mL), dried (Na2SO4) and concentrated to give the crude boronic acid (232 mg). Flash chromatography (20 g SiO2, AcOEt/heptane 1:4?1:2) provided a mixture of 4- and 5-indane boronic acid (123 mg, 44%).

Reference： [1]Patent: US2008/280891,2008,A1 .Location in patent: Page/Page column 27

36
[ 32202-61-2 ]
[ 6134-53-8 ]

Yield	Reaction Conditions	Operation in experiment
15%		Step 1 : 4-BromoindanTo a thick mixture of 4-aminoindan (2.66 g, 20 mmol) in 48percent tetrafluoroboric acid (20 ml) cooled in an ice bath was added a solution of sodium nitrite (1.6 g, 23 mmol) in water (20 ml) over 10 minutes. The mixture was stirred in ice for 10 minutes and was filtered and the filter cake was washed with cold 5percent tetrafluoroboric acid (10 ml) and then with cold water (10 ml). The filter cake was added in portions to copper (II) bromide (5.6 g, 25 mmol) in dimethyl sulfoxide (50 ml). The mixture was stirred for 30 minutes and was added to water (150ml). The mixture was extracted with ethyl acetate (150 ml) and the organic layer was washed with water. The organic layer was dried over magnesium sulfate and was filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using heptane to give the title compound (0.6g, 15percent).

Reference： [1]Patent: WO2011/34828,2011,A1 .Location in patent: Page/Page column 44

37
[ 6134-53-8 ]
tert-butyl 2-((S)-2-((R)-(2,3-dihydro-1H-inden-4-yl)(hydroxy)methyl)-5-oxopyrrolidin-1-yl)ethylcarbamate [ No CAS ]

Reference： [1]Patent: WO2015/24878,2015,A1

38
[ 6134-53-8 ]
(R)-((S)-1-(2-(tert-butoxycarbonylamino)ethyl)-5-oxopyrrolidin-2-yl)(2,3-dihydro-1H-inden-4-yl)methyl methanesulfonate [ No CAS ]

Reference： [1]Patent: WO2015/24878,2015,A1

39
[ 6134-53-8 ]
(1S,8aS)-tert-butyl 1-(2,3-dihydro-1H-inden-4-yl)-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/24878,2015,A1

40
[ 6134-53-8 ]
(1S,8aS)-1-(2,3-dihydro-1H-inden-4-yl)hexahydropyrrolo[1,2-a]pyrazin-6(7H)-one [ No CAS ]

Reference： [1]Patent: WO2015/24878,2015,A1

41
[ 6134-53-8 ]
(1S,8aS)-N-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl)-1-(2,3-dihydro-1H-inden-4-yl)-N-methyl-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/24878,2015,A1

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(1S,8aS)-1-(2,3-dihydro-1H-inden-4-yl)-N-((R)-1-(3-ethyl-5-(trifluoromethyl)phenyl)ethyl)-N-methyl-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/24878,2015,A1

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(1S,8aS)-1-(2,3-dihydro-1H-inden-4-yl)-N-((R)-1-(3-isopropyl-5-(trifluoromethyl)phenyl)ethyl)-N-methyl-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/24878,2015,A1

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(S)-tert-butyl 1,6-dioxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate [ No CAS ]
(S)-tert-butyl 2-(2-(2,3-dihydro-1H-indene-4-carbonyl)-5-oxopyrrolidin-1-yl)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		To a solution of intermediate 144 (1.7 g, 12.39 mmol) in THF (40 mL) at -70 C was added n-BuLi (1.6 M in hexane) (7.52 mL, 12.036mmol) dropwise over 5 min by syringe along the wall of the flask. After adding, the reaction was stirred at this temperature for 30 min. Then the resulting solution was added into a solution of (S)-tert-butyl 1,6- dioxohexahydropyrrolo[l,2-a]pyrazine-2(lH)-carboxylate (3 g, 11.8 mmol) in THF (40 mL). After stirred at -70C for 5 min, the reaction mixture was quenched with saturated NH4CI and extracted with EtOAc (2 x 20 mL), washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give the title compound (1.6 g, yield : 41%); m/z (ES+) : 373 [M+H]+.

Reference： [1]Patent: WO2015/24878,2015,A1 .Location in patent: Page/Page column 110; 111

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[ 73183-34-3 ]
[ 1252793-57-9 ]