Water → [6-(2-Benzoxazole-2-yl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine

HRID 1854618ノート

反応式

HRID 1854618 の反応式
I[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.[O:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[CH:22]1.O(C(C)(C)C)[Li].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1

参加物

7

反応物 4

HCID 962WaterHCID 9228BenzoxazoleHCID 53311312HCID 53311312、化合物HCID 178506942HCID 178506942、化合物

生成物 1

HCID 53312246[6-(2-Benzoxazole-2-yl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine収率 12.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A sealed tube with a teflon screw cap was charged with a mixture of [6-(2-iodo-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (100 mg, 0.264 mmol), benzoxazole (31 mg, 0.264 mmol), Pd(PPh3)4 (15 mg, 0.013 mmol) and LiOtBu (42 mg, 0.529 mmol) in dry dioxane (5 ml) and heated to 100° C. for 24 h. The cooled mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2 eluting with 30% EtOAc in cyclohexane to afford the title compound as a beige solid (12 mg, 12%). 1H NMR (400 MHz, DMSO-d6) δ 9.88 (s, 1H), 8.14-8.11 (m, 2H), 7.99-7.88 (m, 3H), 7.83 (t, J=7.9 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.61-7.51 (m, 2H), 7.46 (d, J=7.3 Hz, 1H), 6.80 (d, J=5.0 Hz, 1H), 2.41 (s, 3H). (ESI+) m/z 370 (M+H)+. Retention time=2.88 mins (method 1).

後処理

  1. extractionextracted with DCM
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure before purification by column chromatography on SiO2 eluting with 30% EtOAc in cyclohexane

出典と根拠

ORDレコード
ord-86f11d124dca4080933a977e4ceece23
出典データセット
uspto-grants-2015_02
特許番号
US08962665B2

反応ノート

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