Sodium Carbonate → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

HRID 1698073ノート

反応式

HRID 1698073 の反応式
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][O:13][C:14]1[N:15]=[CH:16][C:17]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:18][CH:19]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 529878072-Bromobenzo[d]thiazol-6-amine

生成物 1

HCID 248035652-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine収率 96.3%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
140 °C

実験手順

A mixture of 2-bromo-1,3-benzothiazol-6-amine (53 mg, 0.23 mmol), 2-methoxy-5-pyridineboronic acid (50 mg, 0.327 mmol), Pd(dppf)Cl2*DCM (8 mg, 0.01 mmol) and sodium carbonate (0.1 g, 1 mmol) in THF/water (9:1, 3 mL) was heated at 140° C. for 10 minutes in a microwave reactor under argon atmosphere. The mixture was filtered and washed with THF/water (9:1). After having added DCM to the filtrate, the organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash column chromatography (20 to 70% ethyl acetate in heptane), to yield the title compound (57 mg) as an off-white solid. 1H NMR (CHLOROFORM-d) δ 8.68 (d, 1H) 8.16 (dd, 1H) 7.74 (d, 1H) 7.06 (d, 1H) 6.70-6.81 (m, 2H) 3.94 (s, 3H) 3.77 (s, 2H); MS m/z (M+H) 258.

後処理

  1. filtrationThe mixture was filtered
  2. washwashed with THF/water (9:1)
  3. additionAfter having added DCM to the filtrate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (20 to 70% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-659e8d2bd817477f9fb1ccc4913eba1b
出典データセット
uspto-grants-2012_04
特許番号
US08163928B2

反応ノート

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