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Sodium Carbonate → Methyl 2-(4-(tert-butoxycarbonyl)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1394869
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HRID 1394869 반응식
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2B2OC(C)(C)C(C)(C)O2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:30]1[CH:31]=[N:32][CH:33]=[CH:34][C:35]=1NC(=O)OC(C)(C)C.[Li+].[Cl-].[C:46]([O-:49])([O-])=[O:47].[Na+].[Na+]>C(O)C.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.C1(C)C=CC=CC=1>[C:1]([O:49][C:46]([C:35]1[CH:30]=[CH:31][N:32]=[CH:33][C:34]=1[C:8]1[NH:9][C:10]2[C:15]([C:7]=1[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2)=[O:47])([CH3:7])([CH3:6])[CH3:2]
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참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 10707388tert-Butyl (3-bromopyridin-4-yl)carbamateHCID 23152432methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate

생성물 1

HCID 69207220Methyl 2-(4-(tert-butoxycarbonyl)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate수율 78.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a mixture 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), tert-butyl 3-bromopyridin-4-ylcarbamate (328 mg, 1.2 mmol) and LiCl (84.8 mg, 2.0 mmol), in ethanol (3 mL) and toluene (3 mL) was added, 2M aqueous Na2CO3 (1.25 mL, 2.5 mmol) solution. The mixture was then degassed by the application of vacuum followed by flushing with N2. Pd(PPh3)4 (58 mg, 0.05 mmol) was then added and the reaction was heated at 80° C. overnight. The resultant mixture was then filtered and concentrated under vacuum, and the product residue was purified by Prep. reverse phase HPLC to afford the title compound as an off-white solid, (170 mg, 38% yield). MS m/z 450(MH+); 1H NMR (300 MHz, CDCl3) δ ppm 1.15-1.33 (m, 13 H) 1.63-1.98 (m, 6 H) 2.45 (m, 1 H) 3.92 (s, 3 H) 6.94 (s, 1 H) 7.75-7.89 (m, 2 H) 8.17 (s, 1H) 8.21 (d, J=5.86 Hz, 1 H) 8.37 (s, 1 H) 8.45 (d, J=5.86 Hz, 1 H) 9.45 (s, 1 H).

후처리

  1. customThe mixture was then degassed by the application of vacuum
  2. customby flushing with N2
  3. filtrationThe resultant mixture was then filtered
  4. concentrationconcentrated under vacuum
  5. customthe product residue was purified by Prep

출처 및 근거

ORD 기록
ord-c550d18cc4f24563ac2f018e82888ebe
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07348425B2

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