Sodium Carbonate → (1SR,3SR)-3-[3-(2-Chloro-6-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol

HRID 383316노트

반응식

HRID 383316 반응식
Br[C:2]1[N:6]2[CH:7]=[C:8]([NH:11][CH:12]3[CH2:17][CH2:16][CH2:15][CH:14]([OH:18])[CH2:13]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[C:22]([O:35][CH3:36])[N:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:19][C:20]1[CH:25]=[C:24]([C:2]2[N:6]3[CH:7]=[C:8]([NH:11][CH:12]4[CH2:17][CH2:16][CH2:15][CH:14]([OH:18])[CH2:13]4)[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:23]=[C:22]([O:35][CH3:36])[N:21]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 497604102-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 68483082(1RS,3RS)-3-(3-Bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol2회

생성물 1

HCID 86644339(1SR,3SR)-3-[3-(2-Chloro-6-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol

시약·촉매·용매 3

HCID 178419050HCID 178419050, 화합물촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

To a solution of 3-trans-RS/RS(3-bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol [intermediate J step 2] (1 eq, 10.1 mmol, 3.4 g), 2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.05 eq, 10.1 mmol, 2.9 g), Na2CO3 (2 eq, 19 mmol, 2 g) in dioxane (45 ml) and water (13.5 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (0.1 eq, 0.96 mmol, 224 mg). The reaction mixture is heated at 95° C. for 16 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by chromatography on silica eluting with 0-10% MeOH in EtOAc to afford the title compound; [M+H]+=343/345.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic portions are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography on silica eluting with 0-10% MeOH in EtOAc

출처 및 근거

ORD 기록
ord-95a853840a7e4c97a2298ceccd3c9ef0
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367662B2

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