Dichloromethane → HCID 21081808, compound

HRID 347553Notes

Reaction equation

[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[C:13](I)[C:6]=12.[CH3:29][N:30]([CH3:34])[CH2:31][C:32]#[CH:33].C(Cl)Cl>C(N(CC)CC)C.C1COCC1.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].[Cu]I>[CH3:29][N:30]([CH3:34])[CH2:31][C:32]#[C:33][C:13]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:2]=2[F:1])[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A stream of Ar was bubbled through a mixture of tert-butyl 4-(2-fluoro-4-nitrophenoxy)-3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (200 mg, 0.4 mmol), N,N-dimethylprop-2-yn-1-amine (66 mg, 0.8 mmol), Pd(dppf)2Cl2:CH2Cl2 (33 mg, 0.04 mmol), and CuI (20 mg) in triethylamine (0.4 mL) and THF (3 mL) for 5 min. The reaction mixture was heated in a sealed tube at 70° C. for 2 h and the solvent was removed in vacuo. The crude compound was purified by flash column chromatography (silica gel, 5% MeOH/EtOAc) to afford the desired product (170 mg, 95%) as a yellow oil. LC/MS(ESI+) m/z 455 (M+H)+.

Workup

customthe solvent was removed in vacuo
customThe crude compound was purified by flash column chromatography (silica gel, 5% MeOH/EtOAc)

Sources & evidence

ORD record: ord-3ef5547b5aaf436389e8b2d6ad615c53
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173031B2

Reaction notes

Loading…