Lithium borohydride → HCID 67405135, compound

HRID 1188672Notes

Reaction equation

HRID 1188672 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-c56f90ab01e3462e8dba88a111771db7
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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