Sodium Iodide → HCID 66736853, compound

HRID 1640537Notes

Reaction equation

HRID 1640537 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][CH:14]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[N:29]=5)[N:24]=[CH:23][CH:22]=4)[O:13][C:12]3=[O:33])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.Br[CH2:44][CH2:45][C:46]([O:48][CH3:49])=[O:47].[Na+].[I-]>C1COCC1>[CH3:49][O:48][C:46](=[O:47])[CH2:45][CH2:44][N:18]([CH2:17][CH2:16][CH:14]1[O:13][C:12](=[O:33])[N:11]([C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)[CH2:15]1)[CH2:19][CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[N:29]=2)[N:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 76934Methyl 3-bromopropanoateHCID 81531DiisopropylethylamineHCID 66736925HCID 66736925, compound

Product 1

HCID 66736853HCID 66736853, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the compound of Example 72 (0.2 g, 0.44 mmol) in THF (3 mL) was treated with DIPEA (0.147 mL, 2 eq.), methyl 3-bromopropionate (0.074 g, 1 eq.) and NaI (0.067 g, 1 eq.). The mixture was heated at 80° C. for 2 h, partitioned between EA and water. The org. phase was dried over MgSO4 and concentrated. The residue was purified by FC (EA) to give the title compound as a yellowish oil (0.1 g, 42% yield).

Workup

  1. custompartitioned between EA and water
  2. dry with materialphase was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by FC (EA)

Sources & evidence

ORD record
ord-d0e04c9ca4fb465ba1e24f9c67e65316
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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