Stannane, tributyl(1-ethoxyethenyl)- → HCID 66900287, compound

HRID 1913209Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[CH:12]=[N:13][N:14]3[C:19]([N:20]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[CH:18][C:17]([CH:37]4[CH2:42][CH2:41][S:40](=[O:44])(=[O:43])[CH2:39][CH2:38]4)=[N:16][C:15]=23)[CH:2]=1.C([Sn](CCCC)(CCCC)[C:50]([O:52][CH2:53][CH3:54])=[CH2:51])CCC>O1CCOCC1.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>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[CH:12]=[N:13][N:14]3[C:19]([N:20]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])=[C:18]([C:50]([O:52][CH2:53][CH3:54])=[CH2:51])[C:17]([CH:37]4[CH2:38][CH2:39][S:40](=[O:44])(=[O:43])[CH2:41][CH2:42]4)=[N:16][C:15]=23)[CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(quinolin-3-yl)-5-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (Int-2b, 210 mg, 0.28 mmol), tributyl(1-ethoxyvinyl)stannane (310 mg, 0.84 mmol) and Pd(Ph3P)4 (31 mg, 0.028 mmol) in anhydrous dioxane (5.0 mL) was heated under argon at 100° C. for 24 h, cooled and concentrated. The residue purified by Biotage (CH2Cl2/EtOAc, 20:1 to 4:1) to give 169 mg (83%) of the title compound as a light brown solid. LC/MS RT=2.58 min (5 min method). Mass calculated for, M+H 724.33, observed 724.33.

Workup

temperaturecooled
concentrationconcentrated
customThe residue purified by Biotage (CH2Cl2/EtOAc, 20:1 to 4:1)

Sources & evidence

ORD record: ord-9b499acfdd1d49a38f2492677a5e25c2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609675B2

Reaction notes

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