Methanol → HCID 136181654, compound

HRID 1064177Notes

Reaction equation

HRID 1064177 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].CO.C[O:10][C:11]([C:13]1[NH:14][C:15]2[CH:16]=[C:17]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:18]=[C:19]3[C:25](=[O:26])[NH:24][N:23]=[CH:22][C:21]=1[C:20]=23)=O.C(N(CC)CC)C>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:31]([O:30][C:28](=[O:29])[NH:27][C:17]1[CH:18]=[C:19]2[C:25](=[O:26])[NH:24][N:23]=[CH:22][C:21]3=[C:13]([C:11](=[O:10])[NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[NH:14][C:15]([CH:16]=1)=[C:20]23)([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 66053N,N-Dimethylethylenediamine2×HCID 1361816128-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester

Product 1

HCID 136181654HCID 136181654, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

Preparation of example 165 was carried out in a manner analogous to step 5 of Example 147, except that N,N-dimethylethylenediamine was substituted for methanol. Thus CO was bubbled through a mixture of Intermediate 147(d) from Example 147 (1.5 g, 3.97 mmol), triethylamine (1.1 mL, 7.92 mmol), N,N-dimethylethylenediamine (0.7 g, 7.94 mmol) and 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) (0.65 g, 0.796 mmol) in N,N-dimethylformamide (30.0 mL). Reaction conditions, work up and silica gel chromatography (eluted with 46:4:25 dichloromethane: methanol: ethyl acetate) were also carried out in an analogous manner and afforded the title compound (1.25 g, 3.02 mmol) in 76% yield.

Workup

  1. customPreparation of example 165
  2. customReaction conditions
  3. washsilica gel chromatography (eluted with 46:4:25 dichloromethane: methanol: ethyl acetate)

Sources & evidence

ORD record
ord-99aff820796b4c92abe04df34d44be2e
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

Loading…