1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528550

반응식

HRID 528550 반응식
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=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.[Br:71][C:72]1[CH:77]=[C:76]([C:78]([F:81])([F:80])[F:79])[CH:75]=[CH:74][C:73]=1I.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:71][C:72]1[CH:77]=[C:76]([C:78]([F:79])([F:80])[F:81])[CH:75]=[CH:74][C:73]=1[N:20]1[CH2:19][CH2:18][O:17][C:16]2[CH:21]=[C:12]([S:9]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=3)[C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:11])=[O:10])[CH:13]=[CH:14][C:15]1=2

참가 물질

7

반응물 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 162440892-Bromo-1-iodo-4-(trifluoromethyl)benzeneHCID 23676156Sodium t-butoxideHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

생성물 1

HCID 897614134-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
130 °C

실험 절차

A microwave vial was charged with INTERMEDIATE M (0.573 g, 1.372 mmol), Xantphos (0.159 g, 0.274 mmol), 2-bromo-1-iodo-4-trifluoromethyl-benzene (0.722 g, 2.059 mmol), Pd2(dba)3 (0.126 g, 0.137 mmol) and sodium tert-butoxide (0.264 g, 2.74 mmol). The mixture was diluted with toluene (13.72 mL), and purged with nitrogen, and stirred at 130° C. in the microwave for 30 minutes. The reaction was diluted with water, and washed with DCM. The organics were dried using a phase separator, and concentrated under a vacuum. The material was then purified via silica gel MPLC, eluting with 0 to 50% ethyl acetate in heptanes to yield 4-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a light yellow solid.

후처리

  1. custompurged with nitrogen
  2. additionThe reaction was diluted with water
  3. washwashed with DCM
  4. customThe organics were dried
  5. concentrationconcentrated under a vacuum
  6. customThe material was then purified via silica gel MPLC
  7. washeluting with 0 to 50% ethyl acetate in heptanes

출처 및 근거

ORD 기록
ord-c6ad699af5fa4ed1b12e61869a444ca2
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346798B2

연결된 노트

불러오는 중…