Styrene → HCID 178435486, compound

HRID 1695689Notes

Reaction equation

HRID 1695689 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]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.[Pd]>[C@H:11]1([NH:10][C:7]2[O:8][CH2:9][C:4]3[CH:3]=[C:2](/[CH:22]=[CH:23]/[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[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

7

Reactant 4

HCID 7501StyreneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 178419299HCID 178419299, compound

Product 1

HCID 178435486HCID 178435486, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of (6-bromo-4H-benzo[d][1,3]oxazin-2-yl)-(R)-indan-1-yl-amine (Example 32) (200 mg, 0.58 mmol), styrene (91 mg, 0.87 mmol), tri(o-tolyl)phosphine (14.2 mg, 0.047 mmol), triethylamine (295 mg, 2.91 mmol) and palladium actetate (5.23 mg, 0.023 mmol) in acetonitrile (5 ml) was heated under reflux conditions for 23 h, evaporated and purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/heptane) to yield the title compound as white solid (34 mg, 16%). MS (ISP): m/e=367.2 (M+H+); m.p. 162° C.

Workup

  1. temperaturewas heated under reflux conditions for 23 h
  2. customevaporated
  3. custompurified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/heptane)

Sources & evidence

ORD record
ord-a3b3e54912824d4cacb56c4ed1adecb3
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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