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

HRID 218050Notes

Reaction equation

HRID 218050 reaction equation
[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

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 59160841Methyl 4-(4-(thiazol-2-yl)-tetrahydro-2h-pyran-4-yl)benzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-cb769e09b88e426284004100cc5b8a99
Source dataset
uspto-grants-2012_06
Patent number
US08198299B2

Reaction notes

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