Sodium Carbonate → Methyl 2-(2-(benzyloxy)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 860731ノート

反応式

HRID 860731 の反応式
C([O-])([O-])=O.[Na+].[Na+].[CH:7]1([C:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=3)[NH:15][C:14]=2B2OC(C)(C)C(C)(C)O2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:35]([O:42][C:43]1[C:48](Br)=[CH:47][CH:46]=[CH:45][N:44]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[Li+].[Cl-]>C(O)C.C1(C)C=CC=CC=1.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>[CH2:35]([O:42][C:43]1[C:48]([C:14]2[NH:15][C:16]3[C:21]([C:13]=2[CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:17]=3)=[CH:47][CH:46]=[CH:45][N:44]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 147124562-Benzyloxy-3-bromopyridineHCID 23152432methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate

生成物 1

HCID 58765212Methyl 2-(2-(benzyloxy)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate収率 70.4%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

2M Na2CO3 (1.25 mL, 2.5 mmol) aqueous solution was added to a suspension of methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate (383 mg, 1.0 mmol), 2-(benzyloxy)-3-bromopyridine (317 mg, 1.2 mmol) and LiCl (84.8 mg, 2.0 mmol), in ethanol (3 mL) and toluene (3 mL). The mixture was degassed by evacuating the reaction flask and then flushing with N2. Pd(PPh3)4 (58 mg, 0.05 mmol) was then added, and the reaction mixture was heated at 80° C. for 6 hr. The reaction mixture was then filtered and concentrated in vacuo, and the resultant residue was purified by silica gel flash chromotagraphy using hexanes to 50% ethyl acetate in hexanes as eluent to afford the title compound as a yellowish solid, (310 mg, 70% yield). MS m/z 441(MH+); 1H NMR (500 MHz, CDCl3) δ ppm 1.32–1.46 (m, 3 H) 1.78–1.93 (m, 5 H) 2.05–2.16 (m, 2 H) 2.96 (m, 1 H) 3.92 (s, 3 H) 5.25 (s, 2 H) 6.39 (t, J=6.87 Hz, 1 H) 7.31–7.41 (m, 6 H) 7.60 (dd, J=7.17, 1.98 Hz, 1 H) 7.71 (d, J=8.55 Hz, 1 H) 7.84 (d, J=8.55 Hz, 1 H) 8.07 (s, 1 H) 10.32 (s, 1 H).

後処理

  1. customThe mixture was degassed
  2. customby evacuating the reaction flask
  3. customflushing with N2
  4. filtrationThe reaction mixture was then filtered
  5. concentrationconcentrated in vacuo
  6. customthe resultant residue was purified by silica gel flash chromotagraphy

出典と根拠

ORDレコード
ord-86a033d247de4feda94217aa3f7cf7ce
出典データセット
uspto-grants-2006_12
特許番号
US07153848B2

反応ノート

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