2-Bromonicotinaldehyde → HCID 86658863, compound

HRID 2194918Notes

Reaction equation

[C:1]([O:5][C:6](=[O:46])[NH:7][CH2:8][CH:9]([C:30]1[CH:35]=[CH:34][C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][C:31]=1[CH3:45])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[Cl:29])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:48]1[N:55]=[CH:54][CH:53]=[CH:52][C:49]=1[CH:50]=[O:51]>>[Cl:29][C:22]1[CH:23]=[C:24]([CH3:28])[CH:25]=[C:26]([Cl:27])[C:21]=1[O:20][CH2:19][CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH:9]([C:30]2[CH:35]=[CH:34][C:33]([C:48]3[C:49]([CH:50]=[O:51])=[CH:52][CH:53]=[CH:54][N:55]=3)=[CH:32][C:31]=2[CH3:45])[CH2:8][NH:7][C:6](=[O:46])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 47149512-Bromonicotinaldehyde

HCID 86658858HCID 86658858, compound

Product 1

HCID 86658863HCID 86658863, compound

Procedure

Prepared according to the procedure described in EXAMPLE 7, step 2 using tert-butyl{3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl}carbamate from EXAMPLE 9, step 1 and commercially available 2-bromonicotinaldehyde as starting materials. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (10 to 75% in 30 min) afforded the desired compound as a colorless oil.

Workup

customPrepared
customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
washeluting with Hex/EtOAc (10 to 75% in 30 min)

Sources & evidence

ORD record: ord-c2b94aae91ff440dbfe99c9e96aa48bd
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334308B2

Reaction notes

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