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[ CAS No. 860624-88-0 ]

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2D
Chemical Structure| 860624-88-0
Chemical Structure| 860624-88-0
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Product Details of [ 860624-88-0 ]

CAS No. :860624-88-0MDL No. :MFCD11845501
Formula : C10H10BrNO2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :256.10Pubchem ID :49758858
Synonyms :

Computed Properties of [ 860624-88-0 ]

TPSA : 38.3 H-Bond Acceptor Count : 3
XLogP3 : 2.5 H-Bond Donor Count : 1
SP3 : 0.30 Rotatable Bond Count : 2

Safety of [ 860624-88-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 860624-88-0 ]

  • Upstream synthesis route of [ 860624-88-0 ]
  • Downstream synthetic route of [ 860624-88-0 ]

[ 860624-88-0 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 860624-88-0 ]
  • [ 860624-91-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2255 - 2258
[2] Patent: WO2008/118724, 2008, A1,
  • 2
  • [ 860624-87-9 ]
  • [ 860624-88-0 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 16 h; 1-(1 ,1-dimethylethyl) 7-methyl 5-bromo-2,3-dihydro-1 H-indole-1 , 7-dicarboxylate (9 g, 25 mmol) was dissolved in trifluoroacetic acid (6 ml.) and stirred at room temperature for 16 hours. Dichloromethane and sodium hydroxide solution (2 M) were added and the organic layer washed twice with sodium hydroxide solution until the aqueous layer pH > 7. The organic layer was then concentrated in vacuo to give 6.5 g (100percent) of the title compound as a brown solid.1 H NMR (400 MHz, DMSO-D6) δ ppm 2.99 (t, J=8.5 Hz, 2 H) 3.61 (t, J=8.4 Hz, 2 H) 3.78 (s, 3 H) 6.72 (s, 1 H) 7.28 (d, J=1 Hz, 1 H) 7.46 (d, J=2 Hz, 1 H); MS m/z 256/258 (1 :1 ratio) (M+1)+ Rt 3.32 min.
100% at 20℃; for 16 h; Inert atmosphere Intermediate 7:Methyl 5-bromo-2,3-dihydro-1 H-indole-7-carboxylate.1 -(1 ,1 -dimethylethyl) 7-methyl 5-bromo-2,3-dihydro-1 H-indole-1 , 7-dicarboxylate (9 g, 25 mmol) was dissolved in trifluoroacetic acid (6 ml.) and stirred at room temperature for 16 hours. Dichloromethane and sodium hydroxide solution (2 M) were added and the organic layer washed twice with sodium hydroxide solution until the aqueous layer pH > 7. The <n="71"/>organic layer was then concentrated in vacuo to give 6.5 g (100percent) of the title compound as a brown solid.1 H NMR (400 MHz, DMSO-d6) δ ppm 2.99 (t, J=8.5 Hz, 2 H) 3.61 (t, J=8.4 Hz, 2 H) 3.78 (s, 3 H) 6.72 (s, 1 H) 7.28 (d, J=1 Hz, 1 H) 7.46 (d, J=2 Hz, 1 H); MS m/z 256/258 (1 :1 ratio) (M+1 )+ Rt 3.32 min.
96% at 25℃; for 16 h; A mixture of methyl 5-bromo-1,N-(t-butoxycarbonyl)indoline-7-carboxylate (19.5 g, 54.7 mmol) in TFA (15 mL) was stirred at 25 °C for 16 hours. TLC (petroleum ether: ethyl acetate=10:1, Rf = 0.35) indicated that starting material was consumed completely and a major new spot with lower polarity was detected. The reaction was diluted with DCM (100 mL) and adjusted to pH=9 with sat. NaHCO3. The organic phase was separated and concentrated under reduced pressure to give compound methyl 5-bromoindoline-7-carboxylate (13.5 g, 96percent yield) as a brown solid. 1H NMR (400 MHz DMSO) = 7.45 (s, 1H), 7.27 (s, 1H), 6.72 (s, 1H), 3.77 (s, 3H), 3.61(m, 2H), 2.99 (m, 2H). ESI-MS (m/z): 260.0 (M+H)+
Reference: [1] Patent: WO2007/62318, 2007, A2, . Location in patent: Page/Page column 38
[2] Patent: WO2008/118724, 2008, A1, . Location in patent: Page/Page column 68-69
[3] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1164 - 1169
[4] Patent: WO2017/120429, 2017, A1, . Location in patent: Page/Page column 268
[5] Patent: US2009/143372, 2009, A1,
[6] Patent: WO2005/67923, 2005, A1, . Location in patent: Page/Page column 38
[7] Patent: WO2006/34317, 2006, A2, . Location in patent: Page/Page column 73
[8] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2255 - 2258
  • 3
  • [ 143262-10-6 ]
  • [ 860624-88-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2255 - 2258
[2] Patent: WO2017/120429, 2017, A1,
[3] Patent: WO2008/118724, 2008, A1,
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1164 - 1169
  • 4
  • [ 197460-40-5 ]
  • [ 860624-88-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2255 - 2258
[2] Patent: WO2017/120429, 2017, A1,
[3] Patent: WO2008/118724, 2008, A1,
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1164 - 1169
  • 5
  • [ 496-15-1 ]
  • [ 860624-88-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2255 - 2258
[2] Patent: WO2017/120429, 2017, A1,
[3] Patent: WO2008/118724, 2008, A1,
  • 6
  • [ 860624-88-0 ]
  • [ 860624-89-1 ]
YieldReaction ConditionsOperation in experiment
88% With manganese(IV) oxide In tetrahydrofuran at 20℃; Inert atmosphere To a solution of 5-Bromo-2,3-dihydro-1 H-indole-7-carboxylic acid methyl ester (11.5 g, 45.1 mmol) in 10OmL THF was added MnO2 (39.2 g, 451 mmol). Then the mixture was stirred overnight at room temperature. The reaction was filtered and the filtrate was concentrated (10 g, 88percent).
82% With manganese(IV) oxide In dichloromethane at 25℃; for 48 h; To a solution of methyl 5-bromoindoline-7-carboxylate (13.5 g, 52.7 mmol) in DCM (160 mL) was added MnO2 (45.8 g, 527 mmol). The mixture was stirred at 25 °C for 48 hours. TLC (petroleum ether : ethyl acetate=10:1, Rf = 0.3) indicated that startingmaterial was consumed completely and a major new spot with higher polarity was detected. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to afford of methyl 5-bromoindole-7-carboxylate (11 g, 82percent yield) as a brown solid. 1H NMR (400 MHz DMSO) = 11.38 (s, 1H), 8.06 (s, 1H), 8.79 (s, 1H), 7.47 (d, J=6 Hz, 1H), 6.56 (d, J=3.6 Hz, 1H), 3.93 (s, 3H). ESI-MS (m/z): 253.9 (M+H)+
80% With manganese(IV) oxide In tetrahydrofuran at 20℃; for 112 h; Methyl 5-bromo-2,3-dihydro-1 H-indole-7-carboxylate (6.5 g, 25 mmol) was dissolved in tetrahydrofuran (100 mL). Activated manganese dioxide (5 μm particle size, 22 g, 250 mmol) was added and the mixture stirred at room temperature for 16 hours. A further 22 g of activated manganese dioxide was added and the reaction stirred for 96 hours. The reaction was then filtered through celite and concentrated in vacuo to give 5.1 g (80percent) of the title compound as a beige solid.1 H NMR (400 MHz, DMSO-D6) δ ppm 3.94 (s, 3 H) 6.58 (d, J=3 Hz, 1 H) 7.48 (d, J=3 Hz1 1 H) 7.8 (d, J=2 Hz, 1 H) 8.07 (d, J=1.8 Hz, 1 H) 11.39 (bs, 1 H); MS m/z 252/254 (1 :1 ratio) (M-1) Rt 3.41 min.
Reference: [1] Patent: WO2008/118724, 2008, A1, . Location in patent: Page/Page column 69
[2] ACS Medicinal Chemistry Letters, 2018,
[3] Patent: WO2017/120429, 2017, A1, . Location in patent: Page/Page column 268
[4] Patent: WO2007/62318, 2007, A2, . Location in patent: Page/Page column 39
[5] Patent: US2009/143372, 2009, A1,
[6] Patent: WO2005/67923, 2005, A1, . Location in patent: Page/Page column 38-39
[7] Patent: WO2006/34317, 2006, A2, . Location in patent: Page/Page column 73
[8] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2255 - 2258
  • 7
  • [ 860624-88-0 ]
  • [ 860624-90-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2255 - 2258
[2] Patent: WO2008/118724, 2008, A1,
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