Sodium Iodide → Tert-butyl 7-iodo-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

HRID 1616903Notes

Reaction equation

HRID 1616903 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]3[CH:15]4[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]4[O:28][C:11]=3[CH:10]=2)O1.CC1C=CC(S(NCl)(=O)=O)=CC=1.[I-:42].[Na+]>C1COCC1.O>[I:42][C:9]1[CH:14]=[CH:13][C:12]2[CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]3[O:28][C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 5238Sodium Iodide2×HCID 31388Tosylchloramide2×HCID 68305718Tert-butyl 7-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

Product 1

HCID 67325186Tert-butyl 7-iodo-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 7-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate (20 g, 0.05 mol) was dissolved in THF (0.4 L) and a solution of Chloramine T (28.1 g, 0.1 mol) in H2O (0.2 L) was added, followed by a solution of sodium iodide (15 g, 0.1 mol) in H2O (0.2 L) over 20 min. After 20 h stirring, of chloramine T (2.8 g, 0.01 mol) and sodium iodide (1.5 g, 0.01 mol) were added. The reaction mixture was stirred for 20 h, the solvent was evaporated, ethyl acetate and H2O were added. The layers were separated, and the organic layer was washed with H2O.

Workup

  1. additionwere added
  2. customthe solvent was evaporated
  3. additionethyl acetate and H2O were added
  4. customThe layers were separated
  5. washthe organic layer was washed with H2O

Sources & evidence

ORD record
ord-25ee48904b534643a9a7140ceb59cdd7
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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