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Quality Control of [ 377091-17-3 ]

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Product Details of [ 377091-17-3 ]

CAS No. :	377091-17-3	MDL No. :	MFCD28047540
Formula :	C₈H₈Br₂O₂	Boiling Point :	-
Linear Structure Formula :	C₆H₃Br₂C₂H₅O₂	InChI Key :	-
M.W :	295.96	Pubchem ID :	-
Synonyms :

Safety of [ 377091-17-3 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Application In Synthesis of [ 377091-17-3 ]

* 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 [ 377091-17-3 ]
Downstream synthetic route of [ 377091-17-3 ]

[ 377091-17-3 ] Synthesis Path-Upstream 1~2

1
[ 377091-17-3 ]
[ 66826-78-6 ]

Reference： [1] Organic Letters, 2001, vol. 3, # 21, p. 3357 - 3360

2
[ 377091-17-3 ]
[ 189035-22-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: With phosphorus tribromide In toluene at 90℃; for 2.5 h; Heating / reflux Stage #2: With sodium hydroxide In water; toluene at 20℃; Stage #3: With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 0.5 h;	2-(2,5-dibromophenoxy)ethanol (4.65 g, 15.7 mmol) was dissolved in toluene (33 mL) with stirring under N₂. PBr₃ (0.67 mL, 7.07 mmol) was added and the resulting mixture heated at 90 ⁰C under reflux condenser under N₂ for 2.5 hours. The mixture was cooled to room temperature with a H₂O bath and IN NaOH (28 mL) was added. The mixture was diluted with Et₂O, shaken, and the layers separated. The organics were washed with H₂O, dried over MgSO₄, filtered, and concentrated on a rotary evaporator. The resulting oil was dissolved in THF (15 mL) with stirring under N₂. The solution was cooled to -75 ⁰C and n-BuLi (9.82 mL of a 1.6 M solution in hexane, 15.7 mmol) was added dropwise. The resulting clear, colorless solution was stirred 30 minutes at -75 ⁰C, and then HOAc (1 mL) was added. The resulting mixture was warmed to room temperature and partitioned between H2O and Et₂O. The organics were washed once with 0.5 M NaOH, once with H₂O, and concentrated on a rotary evaporator. Flash chromatography <n="145"/>(5-10percent EtOAc/hexane) gave 1.38 g (90percent purity) (40percent yield) of 6-bromo-2,3- dihydrobenzofuran as a white solid. R_f= 0.56 (30percent EtOAc/hexane). ¹H NMR (300 MHz, DMSO-D6) δ ppm 3.13 (t, J=8.52 Hz, 2 H) 4.56 (t, J=8.79 Hz, 2 H) 6.95 - 7.01 (m, 2 H) 7.14 - 7.20 (m, 1 H).

Reference： [1] Patent: WO2007/84560, 2007, A2, . Location in patent: Page/Page column 143-144
[2] Patent: EP2862571, 2015, A1,
[3] Patent: US2015/166559, 2015, A1,
[4] Patent: TW2016/2105, 2016, A,

[ 377091-17-3 ] Synthesis Path-Downstream 1~88

1
[ 377091-17-3 ]
[ 66826-78-6 ]

Reference： [1]Organic Letters,2001,vol. 3,p. 3357 - 3360

2
[ 377091-17-3 ]
[ 189035-22-1 ]

Yield	Reaction Conditions	Operation in experiment
40%		2-(2,5-dibromophenoxy)ethanol (4.65 g, 15.7 mmol) was dissolved in toluene (33 mL) with stirring under N2. PBr3 (0.67 mL, 7.07 mmol) was added and the resulting mixture heated at 90 0C under reflux condenser under N2 for 2.5 hours. The mixture was cooled to room temperature with a H2O bath and IN NaOH (28 mL) was added. The mixture was diluted with Et2O, shaken, and the layers separated. The organics were washed with H2O, dried over MgSO4, filtered, and concentrated on a rotary evaporator. The resulting oil was dissolved in THF (15 mL) with stirring under N2. The solution was cooled to -75 0C and n-BuLi (9.82 mL of a 1.6 M solution in hexane, 15.7 mmol) was added dropwise. The resulting clear, colorless solution was stirred 30 minutes at -75 0C, and then HOAc (1 mL) was added. The resulting mixture was warmed to room temperature and partitioned between H2O and Et2O. The organics were washed once with 0.5 M NaOH, once with H2O, and concentrated on a rotary evaporator. Flash chromatography <n="145"/>(5-10% EtOAc/hexane) gave 1.38 g (90% purity) (40% yield) of 6-bromo-2,3- dihydrobenzofuran as a white solid. Rf= 0.56 (30% EtOAc/hexane). 1H NMR (300 MHz, DMSO-D6) delta ppm 3.13 (t, J=8.52 Hz, 2 H) 4.56 (t, J=8.79 Hz, 2 H) 6.95 - 7.01 (m, 2 H) 7.14 - 7.20 (m, 1 H).

Reference： [1]Patent: WO2007/84560,2007,A2 .Location in patent: Page/Page column 143-144
[2]Patent: EP2862571,2015,A1
[3]Patent: TW2016/2105,2016,A

3
[ 377091-17-3 ]
[ 55745-96-5 ]

Reference： [1]Patent: EP2862571,2015,A1
[2]Patent: WO2017/144633,2017,A1
[3]Patent: WO2017/144639,2017,A1
[4]Patent: WO2017/144635,2017,A1
[5]Patent: WO2019/37861,2019,A1
[6]Patent: WO2019/37860,2019,A1
[7]Patent: WO2020/39029,2020,A1
[8]Patent: WO2020/39028,2020,A1

4
[ 377091-17-3 ]
5-amino-2,3-dihydrobenzofuran-6-formaldehyde [ No CAS ]

Reference： [1]Patent: EP2862571,2015,A1
[2]Patent: US2015/166559,2015,A1

5
[ 377091-17-3 ]
(S)-7-ethyl-7-hydroxy-10,13-dihydro-2H-furo[2,3-g]pyrano[3′,4′:6,7]indolizino [1,2-b]quinoline-8,11(3H,7H)-dione [ No CAS ]

Reference： [1]Patent: EP2862571,2015,A1
[2]Patent: US2015/166559,2015,A1

6
[ 377091-17-3 ]
C₉H₇NO₄ [ No CAS ]

Reference： [1]Patent: EP2862571,2015,A1
[2]Patent: US2015/166559,2015,A1

7
[ 377091-17-3 ]
2-(2,3-dihydrobenzofuran-6-yl)ethan-1-ol [ No CAS ]

Reference： [1]Patent: TW2016/2105,2016,A

8
[ 377091-17-3 ]
2-(2-(2,3-dihydrobenzofuran-6-yl)ethyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: TW2016/2105,2016,A

9
[ 377091-17-3 ]
2-(2,3-dihydrobenzofuran-6-yl)ethanamine [ No CAS ]

Reference： [1]Patent: TW2016/2105,2016,A

10
[ 377091-17-3 ]
1-(2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)ethan-1-one [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

11
[ 377091-17-3 ]
2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

12
[ 377091-17-3 ]
2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-5-methyl-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

13
[ 377091-17-3 ]
2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

14
[ 377091-17-3 ]
2-(4-(1-(2,3-dihydrobenzofuran-7-yl)ethyl) piperazin-1-yl)-5-trityl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1

15
[ 377091-17-3 ]
2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

16
[ 377091-17-3 ]
(S)-2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine [ No CAS ]
(R)-2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

17
[ 377091-17-3 ]
1-(2,3-dihydrobenzofuran-6-yl)ethan-1-ol [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1
[3]Patent: WO2017/144635,2017,A1
[4]Patent: WO2019/37861,2019,A1
[5]Patent: WO2019/37860,2019,A1
[6]Patent: WO2020/39029,2020,A1
[7]Patent: WO2020/39028,2020,A1

18
[ 377091-17-3 ]
N-(1-(1-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperidin-4-yl)-1H-pyrazol-4-yl)acetamide [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

19
[ 377091-17-3 ]
(1-(1-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperidin-4-yl)-1H-pyrazol-4-yl)methanol [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

20
[ 377091-17-3 ]
1-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)piperidine [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

21
[ 377091-17-3 ]
ethyl 1-(1-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperidin-4-yl)-1H-pyrazole-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

22
[ 377091-17-3 ]
6-(1-chloroethyl)-2,3-dihydrobenzofuran [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1
[3]Patent: WO2019/37861,2019,A1
[4]Patent: WO2019/37860,2019,A1
[5]Patent: WO2020/39029,2020,A1
[6]Patent: WO2020/39028,2020,A1

23
[ 377091-17-3 ]
(2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)pyrimidin-5-yl)methanol [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

24
[ 377091-17-3 ]
1-(2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)pyrimidin-5-yl)cyclopropan-1-ol [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

25
[ 377091-17-3 ]
2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-5-methylpyrimidine [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

26
[ 377091-17-3 ]
methyl 2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)pyrimidine-5-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

27
[ 377091-17-3 ]
2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)pyrimidine-5-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

28
[ 377091-17-3 ]
tert-butyl 4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1
[3]Patent: WO2019/37860,2019,A1

29
[ 377091-17-3 ]
1-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperidin-4-yl methanesulfonate [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1

30
[ 377091-17-3 ]
1-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperidin-4-ol [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1
[2]Patent: WO2017/144639,2017,A1
[3]Patent: WO2019/37860,2019,A1

31
[ 377091-17-3 ]
7-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-2H-pyrido[4,3-b][1,4]oxazin-3(4H)-one [ No CAS ]

Reference： [1]Patent: WO2017/144633,2017,A1

32
[ 377091-17-3 ]
2-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-5-trityl-4,5,6, 7-tetrahydrothiazolo[5,4-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

33
[ 377091-17-3 ]
3-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-6-iodopyridazine [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

34
[ 377091-17-3 ]
3-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-6-(trifluoromethyl)pyridazine [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

35
[ 377091-17-3 ]
3-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-6-(methylsulfonyl)pyridazine [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

36
[ 377091-17-3 ]
1-(5-bromopyridin-2-yl)-4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazine [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

37
[ 377091-17-3 ]
(5-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-1,3,4-thiadiazol-2-yl)methanol [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

38
[ 377091-17-3 ]
ethyl 5-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-1,3,4-thiadiazole-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

39
[ 377091-17-3 ]
(5-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-1,3,4-thiadiazol-2-yl)methyl methanesulfonate [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

40
[ 377091-17-3 ]
1-(5-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-1,3,4-thiadiazol-2-yl)-N,N-dimethylmethanamine [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

41
[ 377091-17-3 ]
(5-(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)-1,3,4-thiadiazol-2-yl)methanamine [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

42
[ 377091-17-3 ]
1-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazine dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2017/144639,2017,A1

43
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

44
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

45
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

46
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-1-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

47
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

48
[ 377091-17-3 ]
6-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-1-(pyridin-2-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

49
[ 377091-17-3 ]
6-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

50
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

51
[ 377091-17-3 ]
(R)-5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine [ No CAS ]
(S)-5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

52
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-1-(pyrimidin-5-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

53
[ 377091-17-3 ]
2-bromo-7-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

54
[ 377091-17-3 ]
7-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-(4-(methylsulfonyl)phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

55
[ 377091-17-3 ]
7-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

56
[ 377091-17-3 ]
N-(7-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)acetamide [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

57
[ 377091-17-3 ]
7-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-amine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

58
[ 377091-17-3 ]
6-((7-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)amino)nicotinonitrile [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

59
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-2-(pyrimidin-2-ylmethyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

60
[ 377091-17-3 ]
5-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)-1-(pyrimidin-2-ylmethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/37861,2019,A1

61
[ 377091-17-3 ]
(4-(1-(2,3-dihydrobenzofuran-6-yl)ethyl)piperazin-1-yl)(pyridin-2-yl)methanone [ No CAS ]