Sodium borohydride → (4-aminomethyl-3-methylphenyl)-(5H,11H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-10-yl)methanone

HRID 558947Notes

Reaction equation

HRID 558947 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([CH3:25])[CH:18]=3)=[O:16])[CH2:6][C:5]=12.[BH4-].[Na+]>[Co](Cl)Cl>[NH2:22][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([C:15]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:16])=[CH:18][C:19]=1[CH3:25]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 251783794-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzonitrile

Product 1

HCID 25178381(4-aminomethyl-3-methylphenyl)-(5H,11H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-10-yl)methanone

Reagents, catalysts & solvents 1

HCID 24288Cobalt(II) chlorideCatalyst

Procedure

Following a similar procedure as described for Example F2, 4-(5H,11H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzonitrile from Example G1 (1.5 g, 4.6 mmol) was treated with cobalt (II) chloride (2.2 g, 9.2 mmol) and sodium borohydride (1.75 g, 46 mmol) to afford a pale yellow solid, yield 680 mg, 44%.

Workup

  1. customto afford a pale yellow solid, yield 680 mg, 44%

Sources & evidence

ORD record
ord-eac13df9132b4781a6f7500b7ddc3b34
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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