4-Iodophenol → (S)-7-(3-chloro-2-fluorophenyl)-3-((3-methyloxetan-3-yl)ethynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

HRID 335999Notes

Reaction equation

HRID 335999 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12](I)[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1.IC1C=CC(O)=CC=1.[Cl:30][C:31]1[C:32]([F:40])=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1.C[Si](C)(C)[C:43]#[C:44][C:45]1([CH3:49])[CH2:48][O:47][CH2:46]1>>[Cl:30][C:31]1[C:32]([F:40])=[C:33]([C:12]2[CH:13]=[C:14]3[C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]4[C:5](=[N:6][CH:7]=[C:2]([C:43]#[C:44][C:45]5([CH3:49])[CH2:48][O:47][CH2:46]5)[CH:3]=4)[O:8][C:9]3=[CH:10][CH:11]=2)[CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 108944-IodophenolHCID 162171583-Chloro-2-fluorophenylboronic AcidHCID 58466209(S)-3-bromo-7-iodo-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amineHCID 58547788Trimethyl((3-methyloxetan-3-yl)ethynyl)silane

Product 1

HCID 53465138(S)-7-(3-chloro-2-fluorophenyl)-3-((3-methyloxetan-3-yl)ethynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

Procedure

The titled compound was synthesized by steps analogous to those described in method AA5 above, but using (S)-3-bromo-7-iodo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (prepared using the same procedures as described in Method CC6 but using 4-iodophenol) 3-chloro-2-fluorophenylboronic acid and trimethyl((3-methyloxetan-3-yl)ethynyl)silane. MS m/z=476.1 [M+H]+. Calculated for C26H19ClFN3O3: 475.11. 1H NMR (400 MHz, DMSO-d6) δ=8.45 (br. s., 1 H), 7.67 (br. s., 2 H), 7.65-7.60 (m, 2H), 7.58-7.50 (m, 1 H), 7.47-7.39 (m, 1 H), 7.38-7.31 (m, 1 H), 4.78 (d, J=5.5 Hz, 4 H), 4.46 (d, J=5.6 Hz, 2 H), 1.66 (s, 3 H)

Workup

  1. customprepared

Sources & evidence

ORD record
ord-78f1354627204e82a3107d20996cb8c6
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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