Aluminium lithium hydride → HCID 66842209, compound

HRID 1158835Notes

Reaction equation

HRID 1158835 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH3:21])=[CH:17][CH:18]=2)[N:13]([CH2:29][C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[CH:31]=2)[CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.O1CCCC1>[C:25]([O:24][C:22](=[O:23])[N:20]([C:16]1[CH:15]=[C:14]2[C:19]([C:11]([S:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH2:3][OH:2])=[CH:12][N:13]2[CH2:29][C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[CH:31]=2)=[CH:18][CH:17]=1)[CH3:21])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66842079HCID 66842079, compound

Product 1

HCID 66842209HCID 66842209, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

i)—A solution of 2-[6-(tert-butoxycarbonyl-methyl-amino)-1-(3,5-difluoro-benzyl)-1H-indol-3-ylsulfanyl]-benzoic acid methyl ester (Example 6, method 1, step ii; 0.163 g, 0.30 mmol) in a mixture of diethyl ether and tetrahydrofuran was treated with lithium aluminium hydride (1 M solution in tetrahydrofuran; 0.3 ml, 0.3 mmol). After 1 h stirring, the reaction mixture was quenched with a saturated aqueous solution of sodium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure. Column chromatography (heptane/ethyl acetate 9:1→2:8) afforded [1-(3,5-difluoro-benzyl)-3-(2-hydroxymethyl-phenylsulfanyl)-1H-indol-6-yl]-methyl-carbamic acid tert-butyl ester (0.146 g).

Workup

  1. customthe reaction mixture was quenched with a saturated aqueous solution of sodium sulfate
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-24c4eaec7fa54cfa9b19e56f65960a5f
Source dataset
uspto-grants-2010_10
Patent number
US07812036B2

Reaction notes

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