1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 24961821, 화합물

HRID 1662853노트

반응식

HRID 1662853 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH2:26]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[C:39](Br)[CH:38]=1)(=[O:36])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:26]([NH:33][S:34]([C:37]1[CH:38]=[CH:39][C:40]([CH3:43])=[C:41]([NH:1][C:2]2[CH:7]=[N:6][C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([S:15](=[O:17])(=[O:16])[NH:18][CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:11][CH:10]=3)=[N:4][CH:3]=2)[CH:42]=1)(=[O:36])=[O:35])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

7

반응물 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7213295N-benzyl-3-bromo-4-methylbenzenesulfonamideHCID 23665647Potassium tert-butoxideHCID 58748706HCID 58748706, 화합물

생성물 1

HCID 24961821HCID 24961821, 화합물수율 58%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

A suspension of intermediate 45 (Example 93) (0.10 g, 0.28 mmol), N-benzyl-3-bromo-4-methyl-benzenesulfonamide (0.10 g, 0.29 mmol), Pd(OAc)2 (5 mg, 0.022 mmol), Xantphos (26 mg, 0.045 mmol) and potassium tert-butoxide (70 mg, 0.63 mmol) in a mixture of dioxane/DNIF (2/1, 3 mL) was sealed in a microwave reaction tube and irradiated with microwave at 150° C. for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM) to afford the title compound (0.10 g, 58%) as a white solid.

후처리

  1. customwas sealed in a microwave reaction tube
  2. customirradiated with microwave at 150° C. for 20 min
  3. customthe cap was removed
  4. filtrationthe resulting mixture filtered
  5. washthe filtered solid washed with DCM
  6. concentrationThe filtrate was concentrated
  7. customthe residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM)

출처 및 근거

ORD 기록
ord-df72e65fef484d8db79887f1aec82288
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030487B2

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