Tetravinylstannane → 2-chloro-N-(1H-indazol-6-yl)-5-vinyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 645704

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[N:28][NH:29]3)=[CH:25][CH:24]=2)[C:5]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.[CH:32]([Sn](C=C)(C=C)C=C)=[CH2:33]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[N:28][NH:29]3)=[CH:25][CH:24]=2)[C:5]2[C:10]([CH:32]=[CH2:33])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-chloro-N-(1H-indazol-6-yl)-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.45 g, 0.8 mmol) in dimethylformamide (2.0 mL) was added tetravinyltin (0.29 mL, 1.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.092 g, 0.08 mmol). After degassing, the mixture was heated at 60° C. for 15 h. before it was diluted with EtOAc, and washed sequentially with Sat. NaHCO3 and brine. The organic extract was dried over Na2SO4 and concentrated to give a crude residue. Purification by flash column chromatography (Hexane/EtOAc=1:1) gave 2-chloro-N-(1H-indazol-6-yl)-5-vinyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.11 g).

Workup

customAfter degassing
additionwas diluted with EtOAc
washwashed sequentially with Sat. NaHCO3 and brine
extractionThe organic extract
dry with materialwas dried over Na2SO4
concentrationconcentrated
customto give a crude residue
customPurification by flash column chromatography (Hexane/EtOAc=1:1)

Sources & evidence

ORD record: ord-f5ee33c6b49a4a03a14cc86261f53e97
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Linked notes

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