Tributylvinyltin → HCID 178435485, compound

HRID 1695684Notes

Reaction equation

HRID 1695684 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([NH:10][C@H:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13][CH2:12]3)[O:8][CH2:9][C:4]=2[CH:3]=1.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C@H:11]1([NH:10][C:7]2[O:8][CH2:9][C:4]3[CH:3]=[C:2]([CH:22]=[CH2:23])[CH:21]=[CH:20][C:5]=3[N:6]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 178419299HCID 178419299, compound

Product 1

HCID 178435485HCID 178435485, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A stirred mixture of (6-bromo-4H-benzo[d][1,3]oxazin-2-yl)-(R)-indan-1-yl-amine (Example 32) (1.03 g, 3.0 mmol), tributyl-(vinyl)-stannane (0.98 g, 3 mmol) and tetrakis-(triphenylphosphine)-palladium (0.07 g, 0.06 mmol) in toluene (30 ml) was heated under reflux conditions for 3 h, evaporated and purified by chromatography (ethyl acetate/heptane) on silica gel to yield the title compound as colorless oil (526 mg, 60%). MS (ISP): m/e=291.2 (M+H+).

Workup

  1. temperaturewas heated under reflux conditions for 3 h
  2. customevaporated
  3. custompurified by chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record
ord-7e39946b6fb64507ad6ed43e5c5166bb
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

Loading…