Iodoethane → HCID 59635742, compound

HRID 2037771Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:9](I)[CH3:10].[F:12][C:13]1[CH:18]=[CH:17][C:16]([C@:19]2([CH2:43][C:44]([OH:47])([CH3:46])[CH3:45])[O:24][C:23](=[O:25])[N:22]([C@H:26]([C:28]3[CH:33]=[CH:32][C:31](B4OC(C)(C)C(C)(C)O4)=[CH:30][CH:29]=3)[CH3:27])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1>>[CH2:9]([N:6]1[C:5](=[O:8])[CH:4]=[CH:3][C:2]([C:31]2[CH:30]=[CH:29][C:28]([C@@H:26]([N:22]3[CH2:21][CH2:20][C@@:19]([C:16]4[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=4)([CH2:43][C:44]([OH:47])([CH3:45])[CH3:46])[O:24][C:23]3=[O:25])[CH3:27])=[CH:33][CH:32]=2)=[CH:7]1)[CH3:10]

Participants

Reactant 3

HCID 6340Iodoethane

HCID 5995285-Bromo-2-hydroxypyridine

HCID 59635794HCID 59635794, compound

Product 1

HCID 59635742HCID 59635742, compound

Procedure

The title compound was prepared following a procedure analogous to that described in Example 628, using 5-bromopyridin-2(1H)-one and ethyl iodide in Step 1 and (S)-6-(4-fluorophenyl)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one in Step 2. LC-MS Method 2 tR=1.205 min, m/z=493.2; 1H NMR (CDCl3) 1.16 (d, 6H), 1.39 (t, 3H), 1.52 (d, 3H), 2.19 (s, 4H), 2.20-2.31 (m, 2H), 2.38-2.50 (m, 1H), 2.90 (m, 1H), 4.04 (m, 2H), 5.69 (m, 1H), 6.66 (d, 1H), 7.00 (m, 4H), 7.18 (d, 2H), 7.30 (m, 2H), 7.41 (s, 1H), 7.51 (d, 1H).

Sources & evidence

ORD record: ord-46cf03f343be48f7923efa45f64db83e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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