Triethylamine → HCID 67111749、化合物

HRID 1177550ノート

反応式

HRID 1177550 の反応式
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27](Br)[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:16]([F:30])[CH:15]=1.C[CH2:32][O:33][C:34](C)=[O:35]>CN(C=O)C.C1COCC1.CO>[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([C:34]([O:33][CH3:32])=[O:35])[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:16]([F:30])[CH:15]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 671120772-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole

生成物 1

HCID 67111749HCID 67111749、化合物

試薬・触媒・溶媒 1

HCID 86634690HCID 86634690、化合物溶媒

反応条件

温度
95 °C

実験手順

Triethylamine (0.32 mL, 2.28 mmol), 1,3-(bis[diphenylphosphino]propane) dichloropalladium(II) (0.051 g, 0.076 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole (0.75 g, 1.90 mmol) were mixed in DMF:THF:MeOH (2:7:2, 11 mL total volume) in a heavy-walled pressure tube. The tube was placed under CO atmosphere (20 psi) and then heated to 95° C. for 16 h. The mixture was cooled to RT and EtOAc (5 mL) was added. The suspension was filtered and the collected solid was washed with EtOAc. The solid obtained was then partitioned between DCM and water, the layers were separated, and the organic layer was dried (MgSO4) and concentrated under vacuum to give methyl 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylate as a white solid.

後処理

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe suspension was filtered
  3. washthe collected solid was washed with EtOAc
  4. customThe solid obtained
  5. customwas then partitioned between DCM and water
  6. customthe layers were separated
  7. dry with materialthe organic layer was dried (MgSO4)
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-a7fd57d762c940adb4d23427f774e080
出典データセット
uspto-grants-2010_11
特許番号
US07842685B2

反応ノート

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