Water → HCID 46898436, compound

HRID 602800Notes

Reaction equation

HRID 602800 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([C:15]([S:30]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Br:39])[CH:34]=3)(=[O:32])=[O:31])([CH:17]3[CH2:29][C:20]4[NH:21][C:22]5[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][C:27]=5[C:19]=4[CH2:18]3)[F:16])=[N:13][N:14]=2)=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[Br:39][C:35]1[CH:34]=[C:33]([S:30]([C:15]([CH:17]2[CH2:29][C:20]3[NH:21][C:22]4[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][C:27]=4[C:19]=3[CH2:18]2)([F:16])[C:12]2[O:11][C:10]([C:7]3[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=3)=[N:14][N:13]=2)(=[O:32])=[O:31])[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 46899291HCID 46899291, compound

Product 1

HCID 46898436HCID 46898436, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 12 mg (0.02 mmol) of (RS, SR) 4-[5-[(3-bromo-benzenesulfonyl)-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,3,4]oxadiazol-2-yl}-benzoic acid methyl ester in 0.5 mL of THF was treated with 3 mg (0.08 mmol) of lithium aluminiumhydride and stirred at RT for one hour. The mixture was treated with a mixture of ice cubes and water and extracted twice with dichlormothane. Drying of the combined organic phases over Na2SO4, filtration and evaporation gave 10 mg (86%) of (RS, SR) (4-{5-[(3-bromo-benzenesulfonyl)-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,3,4]oxadiazol-2-yl}-phenyl)-methanol as a yellow solid, MS: 618 (MH+, 1Br).

Workup

  1. extractionextracted twice with dichlormothane
  2. dry with materialDrying of the combined organic phases over Na2SO4, filtration and evaporation

Sources & evidence

ORD record
ord-ebf422be6fe54d27854854734bef9c00
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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