3-Chloro-4-fluoroaniline → 2-(3-Chloro-4-fluorophenylamino)-6-(3-acetamidophenyl)-pyrazine

HRID 16259

反応式

HRID 16259 の反応式
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[F:26])[NH2:22].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:20]=[C:21]([NH:22][C:13]2[N:12]=[C:11]([C:7]3[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=3)[CH:16]=[N:15][CH:14]=2)[CH:23]=[CH:24][C:25]=1[F:26]

参加物

6

反応物 4

HCID 97083-Chloro-4-fluoroanilineHCID 634876Binap, (A+-)-HCID 116874302-(3-Acetamidophenyl)-6-chloropyrazineHCID 23676156Sodium t-butoxide

生成物 1

HCID 116819392-(3-Chloro-4-fluorophenylamino)-6-(3-acetamidophenyl)-pyrazine収率 4.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Using Method K. 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 3-chloro-4-fluoroaniline (42 mg, 0.29 mmol), Pd(0)2 dba3 (9 mg, 0.01 mmol), BINAP (50 mg, 0.04 mmol), sodium tert-butoxide (33 mg, 0.34 mmol) and toluene (5 mL) were reacted at 80° C. for 12 hours. The same workup as for Method K and a combination of column chromatography and preparative TLC furnished 4 mg of title compound. Yield: 4.7%. 1H NMR (250 MHz, DMSO-d6) δ 2.09 (s, 3 H), 7.38 (d, 1 H, J=9.5 Hz), 7.46 (d, 1 H. J=7.9 Hz), 7.61 (d, 1 H, J=7.9 Hz), 7.72 (d, 1 H, 7.5 Hz), 7.86-7.91 (m, 1 H), 8.00-8-04 (m, 1H), 8.18 (s, 1 H), 8.40 (bs, 1 H), 8.48 (s, 1 H), 9.80 (s, 1 H), 10.08 (s, 1 H); m/z 357.2 [(M+H)+, calcd for C18H14ClFN4O 356.1].

出典と根拠

ORDレコード
ord-6ec4dd83266f40fb9157c9f95d575305
出典データセット
uspto-grants-2010_06
特許番号
US07737152B2

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