(6-Fluoropyridin-3-yl)boronic acid → (S)-3-(6,6-dimethyl-3,6-dihydro-2H-pyran-4-yl)-7-(6-fluoropyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

HRID 335996Notes

Reaction equation

HRID 335996 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[CH:13]=[C:12](Cl)[N:11]=[CH:10][C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[F:22][C:23]1[N:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.[CH3:32][C:33]1([CH3:48])[O:38][CH2:37][CH2:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34]1>>[CH3:32][C:33]1([CH3:48])[O:38][CH2:37][CH2:36][C:35]([C:12]2[N:11]=[CH:10][C:9]3[O:8][C:5]4[C:4]([C@@:15]5([CH2:19][O:18][C:17]([NH2:20])=[N:16]5)[C:14]=3[CH:13]=2)=[CH:3][C:2]([C:26]2[CH:27]=[N:28][C:23]([F:22])=[CH:24][CH:25]=2)=[CH:7][CH:6]=4)=[CH:34]1

Participants

4

Reactant 3

HCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 58466134(S)-7-bromo-3-chloro-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amineHCID 585467722-(6,6-dimethyl-3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 53465066(S)-3-(6,6-dimethyl-3,6-dihydro-2H-pyran-4-yl)-7-(6-fluoropyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Procedure

The titled compound was synthesized by steps analogous to those described in method AA1 above, but using (S)-7-bromo-3-chloro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (prepared as described in Method BB41), 6-fluoropyridin-3-ylboronic acid and 2-(6,6-dimethyl-3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. MS m/z=459.0 [M+H]+. Calculated for C26H23FN4O3: 458.18 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.38 (d, J=2.93 Hz, 6 H) 2.53-2.60 (m, 2 H) 3.96 (t, J=5.38 Hz, 2 H) 4.36 (d, J=6.46 Hz, 2 H) 4.55-4.66 (m, 2 H) 6.56 (s, 1 H) 6.98-7.04 (m, 1 H) 7.28 (d, J=8.61 Hz, 1 H) 7.38 (s, 1 H) 7.45-7.53 (m, 1 H) 7.55 (d, J=2.35 Hz, 1 H) 7.87-8.04 (m, 1 H) 8.41 (d, J=2.35 Hz, 1 H) 8.50 (s, 1 H)

Sources & evidence

ORD record
ord-0b8188f7eb834b43849df30c4f9792f8
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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