6-Bromo4-(3-chloro-4-fluoroanilino)quinazoline hydrochloride salt → HCID 22478426, compound

HRID 2184671Notes

Reaction equation

HRID 2184671 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][CH:24]=[C:23]1B(OC(C)C)OC(C)C>>[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:23]3[S:22][CH:26]=[CH:25][CH:24]=3)[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 224783756-Bromo4-(3-chloro-4-fluoroanilino)quinazoline hydrochloride saltHCID 22478406HCID 22478406, compound

Product 1

HCID 22478426HCID 22478426, compoundYield 36%

Procedure

Using an analogous procedure to that described in Example 5 except that the reaction mixture was heated to reflux for 3 hours, 6-bromo-4-(3-chloro-4-fluoroanilino)quinazoline hydrochloride salt was reacted with di-isopropyl 2-thienylboronate to give 4-(3-chloro-4-fluoroanilino)-6-(2-thienyl)quinazoline in 36% yield, m.p. 205-208° C.; NMR Spectrum: 7.2 (m, 1H), 7.4 (t, 1H), 7.7 (m, 2H), 7.8 (m, 2H), 8.15 (m, 2H), 8.55 (s, 1H), 8.75 (d, 1H), 10.0 (broad s, 1H); Elemental Analysis: Found C, 58.6; H, 3.1; N, 11.3; C18H11ClFN3S 0.75H2O requires C, 53.5; H, 3.4; N, 11.4%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours

Sources & evidence

ORD record
ord-b9e5da1768f94934b3894299b15d57e9
Source dataset
uspto-grants-2002_06
Patent number
US06399602B1

Reaction notes

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