8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro(4.5)dec-7-ene → HCID 54772204, compound

HRID 2175578Notes

Reaction equation

HRID 2175578 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(OC1C=CC(Br)=NC=1)C1C=CC=CC=1.CC1(C)C(C)(C)OB(C2CCC3(OCCO3)CC=2)O1.[NH:49]1[CH2:52][CH:51]([NH:53][C:54](=[O:71])[CH2:55][NH:56][C:57]2[C:66]3[C:61](=[CH:62][CH:63]=[C:64]([C:67]([F:70])([F:69])[F:68])[CH:65]=3)[N:60]=[CH:59][N:58]=2)[CH2:50]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([N:49]3[CH2:50][CH:51]([NH:53][C:54](=[O:71])[CH2:55][NH:56][C:57]4[C:66]5[C:61](=[CH:62][CH:63]=[C:64]([C:67]([F:68])([F:70])[F:69])[CH:65]=5)[N:60]=[CH:59][N:58]=4)[CH2:52]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=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 160946965-(Benzyloxy)-2-bromopyridineHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamideHCID 68003660HCID 68003660, compound

Product 1

HCID 54772204HCID 54772204, compound

Procedure

Reaction of 4-(5-hydroxypyridin-2-yl)cyclohexanone (prepared by the reaction of 5-(benzyloxy)-2-bromopyridine 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-b7514e6e75734e3c940d5e540cc7ca2e
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

Loading…