HCID 117667652, compound → HCID 117667552, compound

HRID 712777Notes

Reaction equation

HRID 712777 reaction equation
FC1C=CN=C2C=1CCCN2.Br[C:13]1[C:14]([F:26])=[C:15]2[C:20](=[N:21][CH:22]=1)[N:19]([C:23]([NH2:25])=[O:24])[CH2:18][CH2:17][CH2:16]2.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[C:37]([C:41]3([OH:47])[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[CH:38]=[N:39][CH:40]=2)O1>>[F:26][C:14]1[C:13]([C:35]2[CH:40]=[N:39][CH:38]=[C:37]([C:41]3([OH:47])[CH2:42][CH2:43][O:44][CH2:45][CH2:46]3)[CH:36]=2)=[CH:22][N:21]=[C:20]2[C:15]=1[CH2:16][CH2:17][CH2:18][N:19]2[C:23]([NH2:25])=[O:24]

Participants

4

Reactant 3

HCID 117667652HCID 117667652, compoundHCID 117667716HCID 117667716, compound2×HCID 123231095HCID 123231095, compound

Product 1

HCID 117667552HCID 117667552, compound

Procedure

5-Fluoro-1,2,3,4-tetrahydro-[1,8]naphthyridine is converted to 6-bromo-5-fluoro-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide according to Step 1 and Step 2 of Example 121. 6-Bromo-5-fluoro-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide is coupled with 4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-tetrahydro-pyran-4-ol (which is prepared according to Step 4 of Example 119) to give the titled product using Suzuki Coupling Method VI.

Sources & evidence

ORD record
ord-5310c7694761485fb73e1be3cb19a06c
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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