Acetate → Tert-butyl 5-[2-(2-chloro-4-pyridinyl)quinazolin-4-yl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 1560024Notes

Reaction equation

HRID 1560024 reaction equation
[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH:9]2[CH2:10][N:11]([c:15]3[n:16][c:17]([Cl:25])[n:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]34)[CH:12]([CH2:13]1)[CH2:14]2.[C:64](=[O:65])([O-:66])[O-:67].[C:79]([O-:80])(=[O:81])[CH3:82].[C:84]([O-:85])(=[O:86])[CH3:87].[CH2:76]([Cl:77])[Cl:78].[CH3:70][O:71][CH2:72][CH2:73][O:74][CH3:75].[Cl:48][c:49]1[n:50][cH:51][cH:52][c:53]([B:55]2[O:56][C:57]([CH3:58])([CH3:59])[C:60]([CH3:61])([CH3:62])[O:63]2)[cH:54]1.[Na+:68].[Na+:69].[Pd+2:83].[c:26]1([CH3:27])[cH:28][cH:29][cH:30][cH:31][c:32]1[P:33]([c:34]1[cH:35][cH:36][cH:37][cH:38][c:39]1[CH3:40])[c:41]1[cH:42][cH:43][cH:44][cH:45][c:46]1[CH3:47]>>[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH:9]2[CH2:10][N:11]([c:15]3[n:16][c:17](-[c:53]4[cH:52][cH:51][n:50][c:49]([Cl:48])[cH:54]4)[n:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]34)[CH:12]([CH2:13]1)[CH2:14]2

Participants

10

Reactant 9

HCID 175Acetate2×HCID 923Sodium ion2×HCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 19660Carbonate IonHCID 80271Tri-o-tolylphosphineHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 51034082-Chloropyridine-4-boronic acid, pinacol esterHCID 578327215-(2-Chloro-quinazolin-4-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Product 1

HCID 57832705Tert-butyl 5-[2-(2-chloro-4-pyridinyl)quinazolin-4-yl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Sources & evidence

ORD record
ord-96ec81b7afaf48d082a00ebdd18ed88a
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (1/10)

Reaction notes

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