2-Bromopropane → HCID 89610400, compound

HRID 1507694Notes

Reaction equation

HRID 1507694 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]=1[C:35]([O-:37])=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([NH+](CC)CC)C.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:52]([CH3:54])[CH3:53]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C:10]=1[C:35]([O:37][CH:52]([CH3:54])[CH3:53])=[O:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 89610615HCID 89610615, compound

Product 1

HCID 89610400HCID 89610400, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred suspension of triethylammonium 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (7) [prepared as example B-step (iv) using ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (6) as starting material] (360 mg, 0.60 mmol) and Cs2CO3 (429 mg, 1.32 mmol) in DMF (3 mL) was added 2-bromopropane (197 μL, 2.10 mmol) and the reaction stirred at 40° C. for 2 h then partitioned between EtOAc (50 mL) and water (20 mL). The organic was separated and washed with water (2×50 mL), brine (2×50 mL), dried (MgSO4), filtered and concentrated in vacuo to afford a yellow oil. The residue was purified by silica gel chromatography (40 g, 20-60% EtOAc in isohexane) to afford isopropyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (8) (108 mg, 33%) as a yellow oil: 1H NMR (400 MHz, DMSO-d6) δ: 7.51-7.43 (m, 2H), 7.43-7.28 (m, 8H), 7.19-7.05 (m, 2 H), 6.96-6.84 (m, 2H), 5.13 (s, 2H), 4.96 (s, 2H), 4.85 (sept., J=6.2 Hz, 1H), 3.78 (s, 3H), 2.72 (s, 3H), 2.71 (s, 3H), 1.10 (d, J=6.2 Hz, 6H).

Workup

  1. customthen partitioned between EtOAc (50 mL) and water (20 mL)
  2. customThe organic was separated
  3. washwashed with water (2×50 mL), brine (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil
  8. customThe residue was purified by silica gel chromatography (40 g, 20-60% EtOAc in isohexane)

Sources & evidence

ORD record
ord-9b56ee331a2349219f8f6439abec23ff
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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