Tributylvinyltin → HCID 18680066, compound

HRID 1633876Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:14]2[CH2:16][CH:15]2[C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][N:23]([CH3:30])[CH:24]3[CH:27]([CH3:29])[CH3:28])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]#[N:13])[CH:8]=[CH:7]2.[CH2:31]([Sn](CCCC)(CCCC)C=C)[CH2:32]CC>C1(C)C=CC=CC=1.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>[CH:27]([CH:24]1[C:25]2[C:20](=[CH:19][CH:18]=[C:17]([CH:15]3[CH2:16][CH:14]3[C:4]3[CH:5]=[C:6]4[C:11](=[C:2]([CH:31]=[CH2:32])[CH:3]=3)[CH:10]=[C:9]([C:12]#[N:13])[CH:8]=[CH:7]4)[CH:26]=2)[CH2:21][CH2:22][N:23]1[CH3:30])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of Example 41A (430 mg, 0.94 mmol) in toluene (10 mL) was treated with tributyl(vinyl)stannane (298 mg, 0.94 mmol), and Pd(PPh3)4 (109 mg, 0.09 mmol), flushed with argon, sealed in a tube, and heated to 100° C. for 20 hours. The mixture was cooled to room temperature, treated with ethyl acetate (10 mL), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% methanol/dichloromethane to provide the desired product.

Workup

customflushed with argon
customsealed in a tube
temperatureThe mixture was cooled to room temperature
additiontreated with ethyl acetate (10 mL)
filtrationfiltered
concentrationconcentrated
customThe concentrate was purified by flash column chromatography on silica gel with 10% methanol/dichloromethane

Sources & evidence

ORD record: ord-11a6cc5b664941419f626af5750fb5ad
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06504031B1

Reaction notes

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