Sodium Carbonate → 5'-(3,5-Dimethylisoxazol-4-yl)spiro[[1,3]dioxolane-2,3'-indolin]-2'-one

HRID 1052953

반응식

HRID 1052953 반응식
[CH3:1][C:2]1[C:6](B(O)O)=[C:5]([CH3:10])[O:4][N:3]=1.Br[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]12[O:25][CH2:24][CH2:23][O:22]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2]>[CH3:1][C:2]1[C:6]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])[C:15]23[O:25][CH2:24][CH2:23][O:22]2)=[C:5]([CH3:10])[O:4][N:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27329225'-Bromospiro[1,3-dioxolane-2,3'-[3H]indol]-2'(1'H)-oneHCID 27343463,5-Dimethylisoxazole-4-boronic acid

생성물 1

HCID 1176683845'-(3,5-Dimethylisoxazol-4-yl)spiro[[1,3]dioxolane-2,3'-indolin]-2'-one수율 60.2%

시약·촉매·용매 2

HCID 53384307Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II)촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
110 °C

실험 절차

A mixture of 3,5-dimethylisoxazol-4-ylboronic acid (159 g, 1.13 mol), dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) (23.6 g, 29 mmol), 5′-bromospiro[[1,3]dioxolane-2,3′-indolin]-2′-one (236 g, 0.87 mol) and Na2CO3 (184 g, 1.7 mol) in dioxane/H2O (1200 mL/300 mL) was heated to 110° C. for 12 h. The mixture was filtered through a pad of celite and concentrated in vacuo. The crude product was dissolved in CH2Cl2 (2 L), then hexane 2 L was added and the mixture was filtered again, the organic phase was concentrated in vacuo to give target product (150 g, 60%). 1H NMR (400 MHz, DMSO-d6): δH 10.56 (s, 1H), 7.31-7.33 (m, 2H), 6.93 (d, J=8.0 Hz, 1H), 4.27-4.35 (m, 4H), 2.35 (s, 3H), 2.18 (s, 3H). MS (ESI) m/e [M+1]+ 287.

후처리

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude product was dissolved in CH2Cl2 (2 L)
  4. additionhexane 2 L was added
  5. filtrationthe mixture was filtered again
  6. concentrationthe organic phase was concentrated in vacuo

출처 및 근거

ORD 기록
ord-72e7937554db43e59b6e0687f4539861
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09393232B2

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