Borane → HCID 67447680, compound

HRID 1853773Notes

Reaction equation

HRID 1853773 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:27])([CH3:26])[C:24]#[N:25])=[CH:19][CH:18]=1.B>>[NH2:25][CH2:24][C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:4]2[C:5]3[C:6]4[CH:16]=[CH:15][S:14][C:7]=4[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]=2[O:2][CH3:1])=[CH:22][CH:21]=1)([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 6331BoraneHCID 67450365HCID 67450365, compound

Product 1

HCID 67447680HCID 67447680, compoundYield 40%

Procedure

Following the procedure outlined for Example 265, 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]-2-methylpropanenitrile (250 mg, 0.67 mmol) was reacted with borane (1.0 M in THF, 10 mL, 10.0 mmol) to afford the desired product (100 mg, 40%) as a yellow solid: ESI MS m/z 379 [C22H22N2O2S+H]+.

Sources & evidence

ORD record
ord-f92264564a554526b706994781418e52
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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