2-Bromo-5-(1,3-oxazol-2-yl)benzaldehyde → HCID 15895425, 화합물

HRID 1637707노트

반응식

HRID 1637707 반응식
B([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([C:20]1[C:24]([CH3:25])=[C:23]([CH3:26])[O:22][N:21]=1)[CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])(=[O:12])=[O:11])(O)O.Br[C:28]1[CH:35]=[CH:34][C:33]([C:36]2[O:37][CH:38]=[CH:39][N:40]=2)=[CH:32][C:29]=1[CH:30]=[O:31]>C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][C:24]1[C:20]([N:13]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[S:10]([C:5]2[C:4]([C:28]3[CH:35]=[CH:34][C:33]([C:36]4[O:37][CH:38]=[CH:39][N:40]=4)=[CH:32][C:29]=3[CH:30]=[O:31])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:12])=[O:11])=[N:21][O:22][C:23]=1[CH3:26]

참가 물질

8

반응물 2

HCID 107059332-Bromo-5-(1,3-oxazol-2-yl)benzaldehydeHCID 11728709B-[2-[[(4,5-dimethyl-3-isoxazolyl)[(2-methoxyethoxy)methyl]amino]sulfonyl]phenyl]Boronic acid

생성물 1

HCID 15895425HCID 15895425, 화합물

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매HCID 10340Sodium Carbonate용매

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온도
85 °C

실험 절차

To the 2-borono-N-(4,5-dimethyl-3-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide and 2-bromo-5-(2-oxazolyl)benzaldehyde (13.32 g, 58.14 mmol, prepared as described in Example 21 of European Patent Application No. 702,012) in 264 ml of toluene and 132 ml of 95% ethanol ("EtOH"), 106 ml 2M aqueous sodium carbonate and tetrakis(triphenylphosphine)palladium(0) (6.11 g, 5.29 mmol) were added and the reaction mixture heated under argon at 85° C. for 4 hrs, cooled and diluted with 250 ml of EtOAc. The organic layer was separated and washed with 100 ml H2O and 50 ml brine, dried and concentrated. The residue was chromatographed on silica gel using 1:1 hexane/EtOAc to afford the title product of this step (16.95 g, 62.7% for two steps) as a colorless gum.

후처리

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with 100 ml H2O and 50 ml brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 1:1 hexane/EtOAc

출처 및 근거

ORD 기록
ord-4667c5e162a44d8eaa4b3b625088fc19
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06043265

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