Sodium Iodide → HCID 178482087, compound

HRID 1743767Notes

Reaction equation

HRID 1743767 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]#[C:10][CH2:11][OH:12])[CH2:5][CH2:4]1.[Br:13][C:14]1[CH:15]=[CH:16][C:17](F)=[N:18][CH:19]=1.C(N(C(C)C)C(C)C)C.[Na+].[I-]>CN(C=O)C>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([N:2]([CH3:1])[C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]#[C:10][CH2:11][OH:12])[CH2:7][CH2:8]2)=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 27831685-Bromo-2-fluoropyridineHCID 178484802HCID 178484802, compound

Product 1

HCID 178482087HCID 178482087, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.67 g (4 mmol) trans-3-(4-Methylamino-cyclohexyl)-prop-2-yn-1-ol, 1.24 ml (12 mmol) of 5-bromo-2-fluoropyridine and 1.76 ml (13.6 mmol) N-ethyldiisopropylamine was heated for 3 h at 80° C. and 24 h at 120° C. The mixture was diluted with 1 ml DMF, treated with a catalytic amount of NaI and heated for 2 days at 120° C. The reaction was cooled, evaporated and partitioned between aqueous saturated NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (NaSO4) and evaporated. Flash chromatography on silica gel (MeCl2/Et2O 97.5:2.5 to 92.5:7.5) gave 0.57 g (44%) of trans-3-{4-[(5-Bromo-pyridin-2-yl)-methyl-amino]-cyclohexyl}-prop-2-yn-1-ol, MS: 323 (MH+, 1Br).

Workup

  1. temperatureheated for 2 days at 120° C
  2. temperatureThe reaction was cooled
  3. customevaporated
  4. custompartitioned between aqueous saturated NaHCO3/Et2O (3×)
  5. washThe organic phases were washed with aqueous 10% NaCl
  6. dry with materialdried (NaSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-4d6063130832484c937127be23d96fe5
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

Loading…