Sodium Bicarbonate → HCID 18434416, compound

HRID 1532779Notes

Reaction equation

HRID 1532779 reaction equation
C1C=C[NH+]=CC=1.[Br:7][Br-]Br.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([C:23]1[CH:24]=[N:25][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][CH:28]=1)(O)[CH2:17][CH2:16][CH2:15]2.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:7][C:17]1[CH2:16][CH2:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][CH3:10])[CH:13]=2)[C:18]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[N:25][CH:24]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18434415HCID 18434415, compound

Product 1

HCID 18434416HCID 18434416, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium bromide perbromide (3.5 g, 12.2 mmol) was added to a solution of 6-methoxy-1-[6-(2-pyrrolidin-1-ylethoxy)pyridin-3-yl]-1,2,3,4-tetrahydronaphthalen-1-ol (3.3 g, 8.9 mmol) in CH2Cl2 (50 mL). The reaction was stirred for 18 h and aqueous NaHCO3 (satd) was added. The aqueous layer was extracted with CH2Cl2 and the combined organic solution was washed with water and brine. The organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography (CHCl3: MeOH, 95:5) provided the desired vinyl bromide (2.65 g, 70%). 1H NMR (250 MHz, CDCl3): δ8.0 (d, J=2.4 Hz, 1 H), 7.41 (dd, J=2.4, 8.4 Hz, 1 H), 6.83 (d, J=8.4 Hz, 1 H), 6.69 (m, 1 H), 6.55 (m, 2 H), 4.92 (t, J=5.8 Hz, 2 H), 3.76 (s, 3 H), 2.94 (m, 6 H), 2.64 (m, 4 H), 1.82 (m, 4 H).

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. washthe combined organic solution was washed with water and brine
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8f61dd568384a1ca1d9c6ce7775e1b3
Source dataset
uspto-grants-2001_03
Patent number
US06204286B1

Reaction notes

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