8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro(4.5)dec-7-ene → HCID 54772206, compound

HRID 1896897Notes

Reaction equation

HRID 1896897 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.BrC1C=CN=CC=1OC.CC1(C)C(C)(C)OB(C2CCC3(OCCO3)CC=2)O1.[NH:44]1[CH2:47][CH:46]([NH:48][C:49](=[O:66])[CH2:50][NH:51][C:52]2[C:61]3[C:56](=[CH:57][CH:58]=[C:59]([C:62]([F:65])([F:64])[F:63])[CH:60]=3)[N:55]=[CH:54][N:53]=2)[CH2:45]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13][CH:12]([N:44]2[CH2:45][CH:46]([NH:48][C:49](=[O:66])[CH2:50][NH:51][C:52]3[C:61]4[C:56](=[CH:57][CH:58]=[C:59]([C:62]([F:63])([F:65])[F:64])[CH:60]=4)[N:55]=[CH:54][N:53]=3)[CH2:47]2)[CH2:11][CH2:10]1

Participants

6

Reactant 5

HCID 36970768-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro(4.5)dec-7-eneHCID 5049666Sodium triacetoxyborohydrideHCID 137936294-Bromo-3-methoxypyridineHCID 68003374HCID 68003374, compoundHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 54772206HCID 54772206, compound

Procedure

Reaction of 4-(3-methoxypyridin-4-yl)cyclohexanone (prepared by the reaction of 4-bromo-3-methoxypyridine with 8-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,4-dioxa-spiro[4.5]dec-7-ene using the sequence described in Example 1 Step A-C) with N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide (as prepared in Example 1 Step G) in the presence of TEA and NaBH(OAc)3 as described in Example 1, Step H afforded the product.

Workup

  1. customafforded the product

Sources & evidence

ORD record
ord-5466d88c4baf4dc3b213f72bd053e46b
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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