Phosphorus oxybromide → HCID 45787814, compound

HRID 1046066Notes

Reaction equation

HRID 1046066 reaction equation
[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.[Br:36][C:37]1[N:38]=[N:39][C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:41][CH:42]=1.C(Cl)(=O)C(C)(C)C.P(Br)(Br)(Br)=O>>[C:43]([C:40]1[N:39]=[N:38][C:37]([C:16]2[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]3[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:34])[CH3:35])([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:9][C:8]3=[O:10])[CH3:12])=[CH:18][CH:17]=2)=[CH:42][CH:41]=1)([CH3:46])([CH3:45])[CH3:44].[Br:36][C:37]1[N:38]=[N:39][C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 24613Phosphorus oxybromideHCID 62493Pivaloyl chlorideHCID 45787814HCID 45787814, compoundHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 2

HCID 45787814HCID 45787814, compoundHCID 58485310HCID 58485310, compound

Procedure

The title compound was prepared from (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborol-an-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one and 3-bromo-6-tert-butylpyridazine following a procedure analogous to that described in Example Step 2. 3-bromo-6-tert-butylpyridazine was prepared from pivaloyl chloride following procedures analogous to those described in Example 4 Steps 1-4 using POBr3 in place of POCl3 in Step 4. LC-MS Method 2 tR=1.208 min, m/z=488.3; 1H NMR (CD3OD) 0.94 (s, 3H), 1.25 (s, 3H), 1.48 (s, 9H), 1.57 (d, 3H), 2.15 (s, 2H), 2.29 (m, 1H), 2.50 (m, 2H), 3.10 (m, 1H), 5.60 (m, 1H), 7.14 (d, 2H), 7.30 (m, 5H), 7.81 (d, 2H), 8.07 (d, 1H), 8.20 (d, 1H)

Sources & evidence

ORD record
ord-dfb707dcb4cc49f0a2a4e5aacf696257
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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