Tributylstannane → HCID 86700868, compound

HRID 881761Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]34[CH2:22][CH2:21][C:17]([CH2:23][OH:24])([CH2:18][CH:19]3Br)[CH2:16][O:15]4)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.CC(N=NC(C#N)(C)C)(C#N)C.CCCC[SnH](CCCC)CCCC>C1(C)C=CC=CC=1.O1CCCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]34[CH2:22][CH2:21][C:17]([CH2:23][OH:24])([CH2:18][CH2:19]3)[CH2:16][O:15]4)=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of (1-(4-(5-aminopyridin-2-yl)phenyl)-6-bromo-2-oxabicyclo[2.2.2]octan-4-yl)methanol (240 mg, 0.617 mmol) in toluene (8 ml) and tetrahydrofuran (8 ml) at 40° C. in a microwave vial under nitrogen, was added the mixture of AIBN (40.5 mg, 0.247 mmol) and Bu3SnH (0.980 ml, 3.70 mmol) in toluene at 40° C. The reaction mixture was heated at 100° C. for 3 hours. Most of solvent was removed by evaporation under vacuum, and the residue was purified by chromotography (heptanes/acetone 1/2) to afford (1-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methanol (60 mg, 31%) as yellow solid. LC/MS, [MS+1] 311.1, RT: 0.80; (Condition E).

Workup

customMost of solvent was removed by evaporation under vacuum
customthe residue was purified by chromotography (heptanes/acetone 1/2)

Sources & evidence

ORD record: ord-0e855b873dd3409c8883f9025a151c30
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993619B2

Reaction notes

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