Sodium Carbonate → 4-tert-butyl-N-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamide

HRID 1924767노트

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HRID 1924767 반응식
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:23])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)O1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1.CN(C=O)C.N#N.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].C(Cl)Cl>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]([NH:11][C:9]2[S:8][C:6]3[C:5]([N:10]=2)=[CH:4][CH:3]=[C:2]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[N:7]=3)=[O:23])=[CH:14][CH:15]=1)([CH3:22])([CH3:21])[CH3:20]

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 58015373N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-tert-butylbenzamide

생성물 1

HCID 445467464-tert-butyl-N-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamide수율 50%

시약·촉매·용매 4

HCID 178418807HCID 178418807, 화합물촉매HCID 947Nitrogen용매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

The titled compound was prepared using a procedure analogous to that described in connection with 9 (Example 9). To a microwave vial, N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-tert-butylbenzamide (4A, 120 mg, 1.0 equivalent) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.2 equivalent) in dioxane (0.17 M) and DMF (0.51 M) was stirred in N2. Followed by addition of Na2CO3 (2 M aqueous solution, 8.0 equivalents) and PdCl2(dppf)/DCM adduct (0.05 equivalent). The mixture was heated at 120° C. for 10 minutes. After cooling to room temperature, the crude mixture was added saturated aqueous NaHCO3 and extracted with EtOAc twice. Combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (SiO2, gradient of 1 to 10% MeOH/CH2Cl2) to give the titled compound 10 (50%) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (s, 9H) 7.61 (d, J=8.59 Hz, 2H) 8.08-8.16 (m, 4H) 8.27 (d, J=1.77 Hz, 2H) 8.72 (d, J=6.06 Hz, 2H) 13.07 (s, 1H); ESI-MS: m/z 389.0 (M+H)+.

후처리

  1. customThe titled compound was prepared
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc twice
  4. dry with materialCombined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (SiO2, gradient of 1 to 10% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-4f85712386314b7b81af2f5603787dac
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178555B2

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