Lithium borohydride → HCID 59205418, compound

HRID 2242388Notes

Reaction equation

HRID 2242388 reaction equation
C([O:3][C:4](=O)[CH:5]([CH3:33])[CH2:6][NH:7][C:8]([C:10]1[N:11]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=2)[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19]#[N:20])=[CH:14][CH:13]=2)=[O:9])C.[BH4-].[Li+]>O1CCCC1.O>[OH:3][CH2:4][CH:5]([CH3:33])[CH2:6][NH:7][C:8]([C:10]1[N:11]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:30])[F:31])[CH:23]=2)[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19]#[N:20])=[CH:14][CH:13]=2)=[O:9]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 685468813-{[5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carbonyl]amino}-2-methylpropionic acid ethyl ester

Product 1

HCID 59205418HCID 59205418, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-{[5-Cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carbonyl]amino}-2-methylpropionic acid ethyl ester (170 mg, 0.36 mmol) was dissolved in dry tetrahydrofuran (10 ml) and lithium borohydride (28 mg, 1.28 mmol) was added and heated to reflux for 90 h. The reaction mixture was diluted with water and extracted with ethyl acetate (2×30 ml), the organic layers were combined and washed with water (20 ml) and saturated sodium chloride solution (20 ml). The organics were dried over magnesium sulphate, filtered and evaporated under reduced pressure to give 5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (3-hydroxy-2-methylpropyl)amide as a pale yellow solid which was purified by preparative HPLC (75 mg, 48%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 90 h
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. washwashed with water (20 ml) and saturated sodium chloride solution (20 ml)
  5. dry with materialThe organics were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d55e5c66fc8c4987a91521c1908cf6ce
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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