Allyltributylstannane → 7-Allyl-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

HRID 858244Notes

Reaction equation

HRID 858244 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([F:19])[CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([O:20]C)[CH:3]=1.[CH2:22]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH2:24]>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH2:24]([C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:19])[CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([OH:20])[CH:3]=1)[CH:23]=[CH2:22]

Participants

4

Reactant 2

HCID 90628AllyltributylstannaneHCID 114281017-Bromo-2-(3-fluoro-4-methoxyphenyl)-5-methoxy-1,3-benzoxazole

Product 1

HCID 1355026417-Allyl-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

Reagents, catalysts & solvents 1

HCID 178424406HCID 178424406, compoundCatalyst

Procedure

The title compound was prepared in substantially the same manner as described in Example 24, Route c, step b, from 7-bromo-2-(3-fluoro-4-methoxyphenyl)-5-methoxy-1,3-benzoxazole; allyltributyltin and dichlorobis(tri-o-tolylphosphine)palladium, followed by demethylation according to Example 20, step e. The desired product was obtained as a light pink solid, m.p. 169–171° C.; MS m/e 284 (M−H)+.

Workup

  1. customThe title compound was prepared in substantially the same manner

Sources & evidence

ORD record
ord-4004eed764c34ac2a9319bdde7e3969c
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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