Lithium borohydride → HCID 67405135, compound

HRID 913744Notes

Reaction equation

HRID 913744 reaction equation
[C:1]([C:3]1[C:4]([C:20]([F:23])([F:22])[F:21])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13](=[CH2:18])[C:14](OC)=[O:15])[C:7]([CH3:19])=[CH:6]2)#[N:2].[Li+].[BH4-]>C1COCC1>[OH:15][CH2:14][CH:13]([CH3:18])[CH2:12][N:8]1[C:9]2[C:5](=[C:4]([C:20]([F:23])([F:21])[F:22])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[CH:6]=[C:7]1[CH3:19]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67403795HCID 67403795, compound

Product 1

HCID 67405135HCID 67405135, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-{[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]methyl}-2-propenoate (Example 350) (0.3 g, 0.93 mmol) in THF (10 mL) was cooled to 0° C. and treated with LiBH4 (0.93 mL, 2M in THF). After overnight, the reaction was quenched and partitioned between EtOAc and water. Drying (MgSO4), filtration, and concentration was followed by radial chromatography (0-90% EtOAc-hexanes gradient) to afford the title compound (0.13 g, 47% yield): 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=8.5 Hz, 1H), 7.47 (d, J=8.5 Hz, 1H), 6.56 (s, 1H), 4.33 (dd, J=14.6, 7.3 Hz, 1H), 3.92 (dd, J=14.6, 7.3 Hz, 1H), 3.52 (br, 2H), 2.50 (s, 3H), 2.19 (m, 1H), 1.56 (br, 1H), 0.97 (d, J=6.8 Hz, 3H); MS (ES) m/z 297 (M+1).

Workup

  1. customthe reaction was quenched
  2. custompartitioned between EtOAc and water
  3. customDrying
  4. filtration(MgSO4), filtration, and concentration

Sources & evidence

ORD record
ord-9b6ee914a4464a6096fe02a4c4bb8e4e
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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