Triethylamine → HCID 136181654, compound

HRID 2375101Notes

Reaction equation

HRID 2375101 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[CH:8]=[C:9]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:10]=[C:11]3[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]=1[C:12]=23)=O.C(N(CC)CC)C.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38]>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:23]([O:22][C:20](=[O:21])[NH:19][C:9]1[CH:10]=[C:11]2[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]3=[C:5]([C:3](=[O:2])[NH:38][CH2:37][CH2:36][N:35]([CH3:39])[CH3:34])[NH:6][C:7]([CH:8]=1)=[C:12]23)([CH3:24])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 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 76.1%

Reagents, catalysts & solvents 2

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

Procedure

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. customReaction conditions
  2. washsilica gel chromatography (eluted with 46:4:25 dichloromethane:methanol:ethyl acetate)

Sources & evidence

ORD record
ord-14f6e6fbcee142a9a9a7d9051a25a792
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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