Boronic acid, 3-thienyl-, bis(1-methylethyl) ester → HCID 22478420, compound

HRID 361353Notes

Reaction equation

HRID 361353 reaction equation
Cl.Br[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=1.[S:22]1[CH:26]=[CH:25][C:24](B(OC(C)C)OC(C)C)=[CH:23]1>>[Cl:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[F:20])[NH:13][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:24]3[CH:25]=[CH:26][S:22][CH:23]=3)[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 22478368Boronic acid, 3-thienyl-, bis(1-methylethyl) esterHCID 224783756-Bromo4-(3-chloro-4-fluoroanilino)quinazoline hydrochloride salt

Product 1

HCID 22478420HCID 22478420, compoundYield 51%

Procedure

Using an analogous procedure to that described in Example 5 except that the reaction mixture was heated to reflux for 2 hours, 6-bromo-4-(3-chloro-4-fluoroanilino)quinazoline hydrochloride salt was reacted with di-isopropyl 3-thienylboronate to give 4-(3-chloro-4-fluoroanilino)-6-(3-thienyl)quinazoline in 51% yield, m.p. 195°-197° C.;

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours

Sources & evidence

ORD record
ord-303b618920054734bf960a7d9c768c2c
Source dataset
uspto-grants-1999_02
Patent number
US05866572

Reaction notes

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