Bromine → methyl 4-(4-(5-bromothiazol-2-yl)-tetrahydro-2H-pyran-4-yl)benzoate

HRID 218050노트

반응식

HRID 218050 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[Br:22]Br>CN(C=O)C>[Br:22][C:5]1[S:1][C:2]([C:6]2([C:12]3[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=3)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)=[N:3][CH:4]=1

참가 물질

4

반응물 2

HCID 24408Bromine2회HCID 59160841Methyl 4-(4-(thiazol-2-yl)-tetrahydro-2h-pyran-4-yl)benzoate

생성물 1

HCID 66619354methyl 4-(4-(5-bromothiazol-2-yl)-tetrahydro-2H-pyran-4-yl)benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To the mixture of methyl 4-(4-(thiazol-2-yl)-tetrahydro-2H-pyran-4-yl)benzoate (570 mg, 1.88 mmol) in DMF (5 mL) was added a 1M solution of bromine in DMF (1.9 mL, 1.88 mmol). After 2 hours, additional 1M solution of bromine in DMF (1.9 mL, 1.88 mmol) was added. The reaction mixture was then concentrated to half its volume and poured into water (25 mL). The resulting solid was filtered and washed with water and dried to give methyl 4-(4-(5-bromothiazol-2-yl)-tetrahydro-2H-pyran-4-yl)benzoate. 1H NMR (400 MHz, dmso-d6): δ 7.99 (d, J=8.0 Hz, 2H); 7.58 (s, 1H); 7.41 (d, J=8.0 Hz, 2H); 3.87 (s, 3H); 3.91-3.84 (m, 2H); 3.73-3.68 (m, 2H); 2.63-2.59 (m, 2H); 2.41-2.37 (m, 2H); MS found for C16H16BrNO3S (m/z): 3840.3 [M++1].

후처리

  1. concentrationThe reaction mixture was then concentrated to half its volume
  2. additionpoured into water (25 mL)
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried

출처 및 근거

ORD 기록
ord-cb769e09b88e426284004100cc5b8a99
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198299B2

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